Mechanistic studies on the aryl-aryl interchange reaction of ArPdL2I (L = triarylphosphine) complexes

Journal of the American Chemical Society

Volumn 119, Issue 51, 1997, Pages 12441-12453

  Goodson, Felix E ^a,b   Wallow, Thomas I ^a,c   Novak, Bruce M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b YALE UNIVERSITY   (United States)

^c IBM ALMADEN RESEARCH CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; MOLECULAR INTERACTION; POLYMERIZATION;

EID: 0031585711     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972554g     Document Type: Article

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95. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
96. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
97. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
98. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
99. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
100. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
101. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
102. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
103. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
104. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
105. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
106. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
107. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
108. For examples of P-C cleavage in palladium compounds, see: (a) Coulson, R. D. J. Chem. Soc., Chem. Commun. 1968, 1530. (b) Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695. (c) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910. (d) Yamane, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Tetrahedron 1973, 29, 955. (e) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021. (f) Kikukawa, K.; Yamane, T.; Ohbe, Y.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1187. (g) Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493. (h) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (i) Nishiguchi, T.; Tanaka, K.; Fukuzumi, K. J. Organomet. Chem. 1980, 193, 37. (j) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (k) Kikukawa, K.; Matsuda, T. J. Organomet. Chem. 1982, 235, 243. (l) Abatjoglou, A. G.; Bryant, D. R. Organometallics 1984, 3, 932. (m) Goel, A. ,. Tetrahedron Lett. 1984, 25, 4599. (n) Goel, A. B. Inorg. Chim. Acta 1984, 84, L25. (o) Ortiz, J. V.; Havlas, Z.; Hoffman, R. Helv. Chim. Acta 1984, 67, 1. (p) Bumagin, N. A.; Bumagina, I. G.; Beletskaya, I. P. Zh. Org. Khim. 1984, 20, 457. (q) Reference 14.
109. For examples of P-C cleavage in nickel compounds, see: (a) Green, M. L. H.; Simth, M. J.; Felkin, H.; Swierczewski, G. J. Chem. Soc., Chem. Commun. 1971, 158. (b) Nakamura, A.; Otsuka, S. Tetrahedron Lett. 1974, 463. (c) Reference 35f. (d) Reference 351.
110. For examples of P-C cleavage in nickel compounds, see: (a) Green, M. L. H.; Simth, M. J.; Felkin, H.; Swierczewski, G. J. Chem. Soc., Chem. Commun. 1971, 158. (b) Nakamura, A.; Otsuka, S. Tetrahedron Lett. 1974, 463. (c) Reference 35f. (d) Reference 351.
111. For examples of P-C cleavage in nickel compounds, see: (a) Green, M. L. H.; Simth, M. J.; Felkin, H.; Swierczewski, G. J. Chem. Soc., Chem. Commun. 1971, 158. (b) Nakamura, A.; Otsuka, S. Tetrahedron Lett. 1974, 463. (c) Reference 35f. (d) Reference 351.
112. For examples of P-C cleavage in nickel compounds, see: (a) Green, M. L. H.; Simth, M. J.; Felkin, H.; Swierczewski, G. J. Chem. Soc., Chem. Commun. 1971, 158. (b) Nakamura, A.; Otsuka, S. Tetrahedron Lett. 1974, 463. (c) Reference 35f. (d) Reference 351.
113. For examples of P-C cleavage in cobalt compounds, see: (a) Reference 35f. (b) Reference 351. (c) Sakatura, T.; Kobayashi, T.; Hayashi, T.; Kawabata, Y.; Tanaka, M.; Ogata, I. J. Organomet. Chem. 1984, 267, 171.
114. For examples of P-C cleavage in cobalt compounds, see: (a) Reference 35f. (b) Reference 351. (c) Sakatura, T.; Kobayashi, T.; Hayashi, T.; Kawabata, Y.; Tanaka, M.; Ogata, I. J. Organomet. Chem. 1984, 267, 171.
115. For examples of P-C cleavage in cobalt compounds, see: (a) Reference 35f. (b) Reference 351. (c) Sakatura, T.; Kobayashi, T.; Hayashi, T.; Kawabata, Y.; Tanaka, M.; Ogata, I. J. Organomet. Chem. 1984, 267, 171.
116. For examples of P-C cleavage in osmium compounds, see: (a) Bradford, C. W.; Nyholm, R. S.; Gainsford, G. J.; Guss, J. M.; Ireland, P. R.; Mason, R. J. Chem. Soc., Chem. Commun. 1972, 87. (b) Bradford, C. W.; Nyholm, R. S. J. Chem. Soc., Dalton Trans. 1973, 529. (c) Deeming, A. J.; Kimber, R. E.; Underhill, M. J. Chem. Soc., Dalton Trans. 1973, 2589. (d) Reference 351.
117. For examples of P-C cleavage in osmium compounds, see: (a) Bradford, C. W.; Nyholm, R. S.; Gainsford, G. J.; Guss, J. M.; Ireland, P. R.; Mason, R. J. Chem. Soc., Chem. Commun. 1972, 87. (b) Bradford, C. W.; Nyholm, R. S. J. Chem. Soc., Dalton Trans. 1973, 529. (c) Deeming, A. J.; Kimber, R. E.; Underhill, M. J. Chem. Soc., Dalton Trans. 1973, 2589. (d) Reference 351.
118. For examples of P-C cleavage in osmium compounds, see: (a) Bradford, C. W.; Nyholm, R. S.; Gainsford, G. J.; Guss, J. M.; Ireland, P. R.; Mason, R. J. Chem. Soc., Chem. Commun. 1972, 87. (b) Bradford, C. W.; Nyholm, R. S. J. Chem. Soc., Dalton Trans. 1973, 529. (c) Deeming, A. J.; Kimber, R. E.; Underhill, M. J. Chem. Soc., Dalton Trans. 1973, 2589. (d) Reference 351.
119. For examples of P-C cleavage in osmium compounds, see: (a) Bradford, C. W.; Nyholm, R. S.; Gainsford, G. J.; Guss, J. M.; Ireland, P. R.; Mason, R. J. Chem. Soc., Chem. Commun. 1972, 87. (b) Bradford, C. W.; Nyholm, R. S. J. Chem. Soc., Dalton Trans. 1973, 529. (c) Deeming, A. J.; Kimber, R. E.; Underhill, M. J. Chem. Soc., Dalton Trans. 1973, 2589. (d) Reference 351.
120. For examples of P-C cleavage in compounds of other metals, see: (a) Blickensderfer, J. R.; Kaesz, H. D. J. Am. Chem. Soc. 1975, 97, 2681. (b) Reference 35i. (c) Reference 37c. (d) Reference 35l. (e) Chakravarty, A. R.; Cotton, F. A. Inorg. Chem. 1985, 24, 3584.
121. For examples of P-C cleavage in compounds of other metals, see: (a) Blickensderfer, J. R.; Kaesz, H. D. J. Am. Chem. Soc. 1975, 97, 2681. (b) Reference 35i. (c) Reference 37c. (d) Reference 35l. (e) Chakravarty, A. R.; Cotton, F. A. Inorg. Chem. 1985, 24, 3584.
122. For examples of P-C cleavage in compounds of other metals, see: (a) Blickensderfer, J. R.; Kaesz, H. D. J. Am. Chem. Soc. 1975, 97, 2681. (b) Reference 35i. (c) Reference 37c. (d) Reference 35l. (e) Chakravarty, A. R.; Cotton, F. A. Inorg. Chem. 1985, 24, 3584.
123. For examples of P-C cleavage in compounds of other metals, see: (a) Blickensderfer, J. R.; Kaesz, H. D. J. Am. Chem. Soc. 1975, 97, 2681. (b) Reference 35i. (c) Reference 37c. (d) Reference 35l. (e) Chakravarty, A. R.; Cotton, F. A. Inorg. Chem. 1985, 24, 3584.
124. For examples of P-C cleavage in compounds of other metals, see: (a) Blickensderfer, J. R.; Kaesz, H. D. J. Am. Chem. Soc. 1975, 97, 2681. (b) Reference 35i. (c) Reference 37c. (d) Reference 35l. (e) Chakravarty, A. R.; Cotton, F. A. Inorg. Chem. 1985, 24, 3584.
125. For examples of phosphine-derived byproducts in catalytic reactions, see: (a) Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. (b) Mitchell, R. H.; Chaudhary, M.; Dingle, T. W.; Williams, R. V. J. Am. Chem. Soc. 1984, 106, 7776. (c) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1984, 3, 649. (d) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1986, 5, 460. (e) Dubois, R. A.; Garrou, P. E. Organometallics 1986, 5, 466. (f) Brenda, M.; Greiner, A.; Heitz, W. Makromol. Chem. 1990, 191, 1083. (g) Reference 17.
126. For examples of phosphine-derived byproducts in catalytic reactions, see: (a) Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. (b) Mitchell, R. H.; Chaudhary, M.; Dingle, T. W.; Williams, R. V. J. Am. Chem. Soc. 1984, 106, 7776. (c) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1984, 3, 649. (d) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1986, 5, 460. (e) Dubois, R. A.; Garrou, P. E. Organometallics 1986, 5, 466. (f) Brenda, M.; Greiner, A.; Heitz, W. Makromol. Chem. 1990, 191, 1083. (g) Reference 17.
127. For examples of phosphine-derived byproducts in catalytic reactions, see: (a) Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. (b) Mitchell, R. H.; Chaudhary, M.; Dingle, T. W.; Williams, R. V. J. Am. Chem. Soc. 1984, 106, 7776. (c) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1984, 3, 649. (d) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1986, 5, 460. (e) Dubois, R. A.; Garrou, P. E. Organometallics 1986, 5, 466. (f) Brenda, M.; Greiner, A.; Heitz, W. Makromol. Chem. 1990, 191, 1083. (g) Reference 17.
128. For examples of phosphine-derived byproducts in catalytic reactions, see: (a) Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. (b) Mitchell, R. H.; Chaudhary, M.; Dingle, T. W.; Williams, R. V. J. Am. Chem. Soc. 1984, 106, 7776. (c) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1984, 3, 649. (d) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1986, 5, 460. (e) Dubois, R. A.; Garrou, P. E. Organometallics 1986, 5, 466. (f) Brenda, M.; Greiner, A.; Heitz, W. Makromol. Chem. 1990, 191, 1083. (g) Reference 17.
129. For examples of phosphine-derived byproducts in catalytic reactions, see: (a) Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. (b) Mitchell, R. H.; Chaudhary, M.; Dingle, T. W.; Williams, R. V. J. Am. Chem. Soc. 1984, 106, 7776. (c) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1984, 3, 649. (d) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1986, 5, 460. (e) Dubois, R. A.; Garrou, P. E. Organometallics 1986, 5, 466. (f) Brenda, M.; Greiner, A.; Heitz, W. Makromol. Chem. 1990, 191, 1083. (g) Reference 17.
130. For examples of phosphine-derived byproducts in catalytic reactions, see: (a) Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. (b) Mitchell, R. H.; Chaudhary, M.; Dingle, T. W.; Williams, R. V. J. Am. Chem. Soc. 1984, 106, 7776. (c) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1984, 3, 649. (d) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1986, 5, 460. (e) Dubois, R. A.; Garrou, P. E. Organometallics 1986, 5, 466. (f) Brenda, M.; Greiner, A.; Heitz, W. Makromol. Chem. 1990, 191, 1083. (g) Reference 17.
131. For examples of phosphine-derived byproducts in catalytic reactions, see: (a) Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499. (b) Mitchell, R. H.; Chaudhary, M.; Dingle, T. W.; Williams, R. V. J. Am. Chem. Soc. 1984, 106, 7776. (c) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1984, 3, 649. (d) Dubois, R. A.; Garrou, P. E.; Lavin, K. D.; Allcock, H. R. Organometallics 1986, 5, 460. (e) Dubois, R. A.; Garrou, P. E. Organometallics 1986, 5, 466. (f) Brenda, M.; Greiner, A.; Heitz, W. Makromol. Chem. 1990, 191, 1083. (g) Reference 17.
132. (a) Reference 40b.
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134. (c) Reference 14c.
135. (d) Reference 14d.
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137. (b) Reference 35h.
138. (c) Reference 35j.
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143. (a) Reference 35p.
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147. (e) Reference 16b.
148. For a discussion on possible mechanistic differences between catalytic and stoichiometric cross-coupling reactions, see ref 34e.
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150. 5]phenyl rings are negligible. A negligible isotope effect is in fact expected due to the at least two-bond separation between the reaction center and a perturbing isotope, as well as the geometry of the aryl ring, and is strongly confirmed by the fidelity of the experimental interchange distributions to the predicted distributions. For a discussion of secondary isotope effects, see: Carpenter, B. K., Determination of Organic Reaction Mechanisms; Wiley: New York, 1984; pp 96-100.
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161. A detailed understanding of how scrambled products arise remains elusive despite careful investigation: (a) Negishi, E.; Takahashi, T.; Akiyoshi, K. J. Organomet. Chem. 1987, 331, 334. In Stille couplings, homocoupling of arylstannanes occurs in the presence of adventitions oxygen: (b) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434. Homocoupled products predominate in certain Suzuki couplings. This can be synthetically useful: (c) Song, Z. Z.; Wong, H. C. J. Org. Chem. 1994, 59, 33.
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