Efficient Stille cross-coupling reaction catalyzed by the Pd(OAc) 2/Dabco catalytic system

Journal of Organic Chemistry

Volumn 70, Issue 7, 2005, Pages 2832-2834

  Li, Jin Heng ^a   Liang, Yun ^a   Wang, De Ping ^a   Liu, Wen Jie ^a   Xie, Ye Xiang ^a   Yin, Du Lin ^a  

^a HUNAN NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AROMATIC COMPOUNDS; OLEFINS; ORGANOMETALLICS; PALLADIUM; REACTION KINETICS;

ALKYNES; ARYL HALIDES; STILLE CROSS COUPLING REACTIONS; TURNOVER NUMBERS (TON);

CATALYSIS;

PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; EVALUATION; LIGAND BINDING;

EID: 17044430638     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048066q     Document Type: Article

References (47)

1. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998. (c) Shirakawa, E.; Hiyama, T. J. Organomet. Chem. 1999, 576, 169. (d) Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002. (e) Hegedus, L. S. In Oranometallics in Synthesis; Schlosser, M., Ed.; J. Wiley & Sons: Chichester, 2002; p 1123. (f) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002. (g) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176. (h) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (i) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
2. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998. (c) Shirakawa, E.; Hiyama, T. J. Organomet. Chem. 1999, 576, 169. (d) Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002. (e) Hegedus, L. S. In Oranometallics in Synthesis; Schlosser, M., Ed.; J. Wiley & Sons: Chichester, 2002; p 1123. (f) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002. (g) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176. (h) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (i) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
3. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998. (c) Shirakawa, E.; Hiyama, T. J. Organomet. Chem. 1999, 576, 169. (d) Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002. (e) Hegedus, L. S. In Oranometallics in Synthesis; Schlosser, M., Ed.; J. Wiley & Sons: Chichester, 2002; p 1123. (f) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002. (g) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176. (h) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (i) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
4. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998. (c) Shirakawa, E.; Hiyama, T. J. Organomet. Chem. 1999, 576, 169. (d) Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002. (e) Hegedus, L. S. In Oranometallics in Synthesis; Schlosser, M., Ed.; J. Wiley & Sons: Chichester, 2002; p 1123. (f) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002. (g) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176. (h) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (i) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
5. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998. (c) Shirakawa, E.; Hiyama, T. J. Organomet. Chem. 1999, 576, 169. (d) Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002. (e) Hegedus, L. S. In Oranometallics in Synthesis; Schlosser, M., Ed.; J. Wiley & Sons: Chichester, 2002; p 1123. (f) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002. (g) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176. (h) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (i) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
6. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998. (c) Shirakawa, E.; Hiyama, T. J. Organomet. Chem. 1999, 576, 169. (d) Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002. (e) Hegedus, L. S. In Oranometallics in Synthesis; Schlosser, M., Ed.; J. Wiley & Sons: Chichester, 2002; p 1123. (f) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002. (g) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176. (h) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (i) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
7. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998. (c) Shirakawa, E.; Hiyama, T. J. Organomet. Chem. 1999, 576, 169. (d) Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002. (e) Hegedus, L. S. In Oranometallics in Synthesis; Schlosser, M., Ed.; J. Wiley & Sons: Chichester, 2002; p 1123. (f) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002. (g) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176. (h) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (i) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
8. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998. (c) Shirakawa, E.; Hiyama, T. J. Organomet. Chem. 1999, 576, 169. (d) Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002. (e) Hegedus, L. S. In Oranometallics in Synthesis; Schlosser, M., Ed.; J. Wiley & Sons: Chichester, 2002; p 1123. (f) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002. (g) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176. (h) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (i) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
9. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998. (c) Shirakawa, E.; Hiyama, T. J. Organomet. Chem. 1999, 576, 169. (d) Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002. (e) Hegedus, L. S. In Oranometallics in Synthesis; Schlosser, M., Ed.; J. Wiley & Sons: Chichester, 2002; p 1123. (f) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002. (g) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176. (h) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (i) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
10. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
11. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
12. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
13. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
14. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
15. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
16. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
17. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
18. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
19. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
20. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
21. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
22. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
23. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
24. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
25. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
26. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
27. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
28. For recent representative papers on phosphine-palladium catalysts, see: (a) Litter, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411. (b) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (c) Litter, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343 and references therein, (d) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696. (e) Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718. (f) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (g) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. (h) Tang, H.; Menzel, K.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5079. (i) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077. (j) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551. (k) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132. (l) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421. (m) Mazzola, R. D., Jr.; Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69, 220. (n) Högenauer, K. Synlett 2001, 878. (o) Scrivanti, A.; Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B. Tetrahedron 2002, 58, 6881. (p) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057. (q) Crocian, B.; Antonaroli, S.; Canovese, L.; Uguagliat, P.; Visentin, F. Eur. J. Inorg. Chem. 2004, 732. (r) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895. (s) Ceccarelli, S.; Piarulli, U.; Gennari, C. J. Org. Chem. 2000, 65, 6254.
29. For recent reviews and papers on N-heterocyclic carbene-palladium catalysts, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (b) Yong, B. S.; Nolan, S. P. Chemtracts: Org. Chem. 2003, 205. (c) Herrmann, W. A.; Öfele, K.; Preysing, D. v.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229. (d) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (e) Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69.
30. For recent reviews and papers on N-heterocyclic carbene-palladium catalysts, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (b) Yong, B. S.; Nolan, S. P. Chemtracts: Org. Chem. 2003, 205. (c) Herrmann, W. A.; Öfele, K.; Preysing, D. v.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229. (d) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (e) Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69.
31. For recent reviews and papers on N-heterocyclic carbene-palladium catalysts, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (b) Yong, B. S.; Nolan, S. P. Chemtracts: Org. Chem. 2003, 205. (c) Herrmann, W. A.; Öfele, K.; Preysing, D. v.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229. (d) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (e) Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69.
32. For recent reviews and papers on N-heterocyclic carbene-palladium catalysts, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (b) Yong, B. S.; Nolan, S. P. Chemtracts: Org. Chem. 2003, 205. (c) Herrmann, W. A.; Öfele, K.; Preysing, D. v.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229. (d) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (e) Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69.
33. For recent reviews and papers on N-heterocyclic carbene-palladium catalysts, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (b) Yong, B. S.; Nolan, S. P. Chemtracts: Org. Chem. 2003, 205. (c) Herrmann, W. A.; Öfele, K.; Preysing, D. v.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229. (d) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119. (e) Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69.
34. For recent representative papers on other phosphine-free ligand-palladium catalysts, see: (a) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (b) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Org. Lett. 2000, 2, 1823. (c) Chouday, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (d) Davis, J. L.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2004, 43, 590. (e) Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212. (f) Minière, S.; Cintrat, J.-C. J. Org. Chem. 2001, 66, 7385. (g) Serrano, J. L.; Fairlamb, I. J. S.; Sánchez, G.; García, L.; Pérez, J.; Vives, J.; López, G.; Crawforth, C. M.; Taylor, R. J. K. Eur. J. Inorg. Chem. 2004, 2706.
35. For recent representative papers on other phosphine-free ligand-palladium catalysts, see: (a) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (b) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Org. Lett. 2000, 2, 1823. (c) Chouday, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (d) Davis, J. L.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2004, 43, 590. (e) Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212. (f) Minière, S.; Cintrat, J.-C. J. Org. Chem. 2001, 66, 7385. (g) Serrano, J. L.; Fairlamb, I. J. S.; Sánchez, G.; García, L.; Pérez, J.; Vives, J.; López, G.; Crawforth, C. M.; Taylor, R. J. K. Eur. J. Inorg. Chem. 2004, 2706.
36. For recent representative papers on other phosphine-free ligand-palladium catalysts, see: (a) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (b) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Org. Lett. 2000, 2, 1823. (c) Chouday, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (d) Davis, J. L.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2004, 43, 590. (e) Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212. (f) Minière, S.; Cintrat, J.-C. J. Org. Chem. 2001, 66, 7385. (g) Serrano, J. L.; Fairlamb, I. J. S.; Sánchez, G.; García, L.; Pérez, J.; Vives, J.; López, G.; Crawforth, C. M.; Taylor, R. J. K. Eur. J. Inorg. Chem. 2004, 2706.
37. For recent representative papers on other phosphine-free ligand-palladium catalysts, see: (a) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (b) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Org. Lett. 2000, 2, 1823. (c) Chouday, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (d) Davis, J. L.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2004, 43, 590. (e) Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212. (f) Minière, S.; Cintrat, J.-C. J. Org. Chem. 2001, 66, 7385. (g) Serrano, J. L.; Fairlamb, I. J. S.; Sánchez, G.; García, L.; Pérez, J.; Vives, J.; López, G.; Crawforth, C. M.; Taylor, R. J. K. Eur. J. Inorg. Chem. 2004, 2706.
38. For recent representative papers on other phosphine-free ligand-palladium catalysts, see: (a) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (b) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Org. Lett. 2000, 2, 1823. (c) Chouday, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (d) Davis, J. L.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2004, 43, 590. (e) Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212. (f) Minière, S.; Cintrat, J.-C. J. Org. Chem. 2001, 66, 7385. (g) Serrano, J. L.; Fairlamb, I. J. S.; Sánchez, G.; García, L.; Pérez, J.; Vives, J.; López, G.; Crawforth, C. M.; Taylor, R. J. K. Eur. J. Inorg. Chem. 2004, 2706.
39. For recent representative papers on other phosphine-free ligand-palladium catalysts, see: (a) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (b) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Org. Lett. 2000, 2, 1823. (c) Chouday, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (d) Davis, J. L.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2004, 43, 590. (e) Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212. (f) Minière, S.; Cintrat, J.-C. J. Org. Chem. 2001, 66, 7385. (g) Serrano, J. L.; Fairlamb, I. J. S.; Sánchez, G.; García, L.; Pérez, J.; Vives, J.; López, G.; Crawforth, C. M.; Taylor, R. J. K. Eur. J. Inorg. Chem. 2004, 2706.
40. For recent representative papers on other phosphine-free ligand-palladium catalysts, see: (a) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (b) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Org. Lett. 2000, 2, 1823. (c) Chouday, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (d) Davis, J. L.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2004, 43, 590. (e) Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212. (f) Minière, S.; Cintrat, J.-C. J. Org. Chem. 2001, 66, 7385. (g) Serrano, J. L.; Fairlamb, I. J. S.; Sánchez, G.; García, L.; Pérez, J.; Vives, J.; López, G.; Crawforth, C. M.; Taylor, R. J. K. Eur. J. Inorg. Chem. 2004, 2706.
41. For a representative paper on diazabutadiene-palladium catalysts [Pd(Ar-BIAN)], see: van Asselt, R.; Elsevier, C. J. Tetrahedron 1994, 50, 323.
42. (a) Pignolet, L. H., Ed. Homogeneous Catalysis with Metal Phosphine Complexes; Plenum: New York, 1983.
43. (b) Parshall, G. W.; Ittel, S. Homogeneous Catalysis; J. Wiley and Sons: New York, 1992.
44. Li, J.-H.; Liu, W.-J. Org. Lett. 2004, 6, 2809.
45. For other papers on amine-palladium catalysts for the Suzuki cross-coupling reaction, see: (a) Tao, B.; Boykin, D. W. Tetrahedron Lett. 2003, 44, 7993. (b) Tao, B.; Boykin, D. W. J. Org. Chem. 2004, 69, 4330.
46. For other papers on amine-palladium catalysts for the Suzuki cross-coupling reaction, see: (a) Tao, B.; Boykin, D. W. Tetrahedron Lett. 2003, 44, 7993. (b) Tao, B.; Boykin, D. W. J. Org. Chem. 2004, 69, 4330.
47. 13C NMR spectra.