Palladium-catalyzed coupling reaction of terminal alkynes with aryl iodides in the presence of indium tribromide and its application to a one-pot synthesis of 2-phenylindole

Organic Letters

Volumn 6, Issue 10, 2004, Pages 1527-1530

  Sakai, Norio ^a   Annaka, Kimiyoshi ^a   Konakahara, Takeo ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLETHYNYLANILINE; 2 PHENYLINDOLE DERIVATIVE; ALKYNE DERIVATIVE; ANILINE DERIVATIVE; BENZENE DERIVATIVE; BROMINE DERIVATIVE; FUNCTIONAL GROUP; INDIUM; INDIUM TRIBROMIDE; INDOLE DERIVATIVE; IODINE DERIVATIVE; PALLADIUM; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; CYCLOADDITION;

EID: 2542623022     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036499u     Document Type: Article

References (69)

1. For selected reviews of metal-catalyzed coupling reactions, see: (a) Negishi, E. Xu, C. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Eds.; Wiley-Interscience: New York, 2002; p 531. (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol 3, p 521. (c) Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979 and refs cited therein.
2. For selected reviews of metal-catalyzed coupling reactions, see: (a) Negishi, E. Xu, C. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Eds.; Wiley-Interscience: New York, 2002; p 531. (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol 3, p 521. (c) Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979 and refs cited therein.
3. For selected reviews of metal-catalyzed coupling reactions, see: (a) Negishi, E. Xu, C. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Eds.; Wiley-Interscience: New York, 2002; p 531. (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol 3, p 521. (c) Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979 and refs cited therein.
4. For selected reviews and papers on the Sonogashira alkynylation and the Heck alkynylation, see: (a) Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Eds.; Wiley-Interscience: New York, 2002; p 493. (b) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566 and refs cited therein. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (d) Takahashi, S.; Kuroyama, K.; Sonogashira, K. Hagihara, N. Synthesis 1980, 627. (e) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467. (f) Dieck, H. A.; Heck, F. R. J. Organomet. Chem. 1975, 93, 259. (g) Cassar, L. J. Organomet. Chem. 1975, 93, 253.
5. For selected reviews and papers on the Sonogashira alkynylation and the Heck alkynylation, see: (a) Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Eds.; Wiley-Interscience: New York, 2002; p 493. (b) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566 and refs cited therein. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (d) Takahashi, S.; Kuroyama, K.; Sonogashira, K. Hagihara, N. Synthesis 1980, 627. (e) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467. (f) Dieck, H. A.; Heck, F. R. J. Organomet. Chem. 1975, 93, 259. (g) Cassar, L. J. Organomet. Chem. 1975, 93, 253.
6. For selected reviews and papers on the Sonogashira alkynylation and the Heck alkynylation, see: (a) Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Eds.; Wiley-Interscience: New York, 2002; p 493. (b) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566 and refs cited therein. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (d) Takahashi, S.; Kuroyama, K.; Sonogashira, K. Hagihara, N. Synthesis 1980, 627. (e) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467. (f) Dieck, H. A.; Heck, F. R. J. Organomet. Chem. 1975, 93, 259. (g) Cassar, L. J. Organomet. Chem. 1975, 93, 253.
7. For selected reviews and papers on the Sonogashira alkynylation and the Heck alkynylation, see: (a) Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Eds.; Wiley-Interscience: New York, 2002; p 493. (b) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566 and refs cited therein. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (d) Takahashi, S.; Kuroyama, K.; Sonogashira, K. Hagihara, N. Synthesis 1980, 627. (e) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467. (f) Dieck, H. A.; Heck, F. R. J. Organomet. Chem. 1975, 93, 259. (g) Cassar, L. J. Organomet. Chem. 1975, 93, 253.
8. For selected reviews and papers on the Sonogashira alkynylation and the Heck alkynylation, see: (a) Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Eds.; Wiley-Interscience: New York, 2002; p 493. (b) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566 and refs cited therein. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (d) Takahashi, S.; Kuroyama, K.; Sonogashira, K. Hagihara, N. Synthesis 1980, 627. (e) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467. (f) Dieck, H. A.; Heck, F. R. J. Organomet. Chem. 1975, 93, 259. (g) Cassar, L. J. Organomet. Chem. 1975, 93, 253.
9. For selected reviews and papers on the Sonogashira alkynylation and the Heck alkynylation, see: (a) Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Eds.; Wiley-Interscience: New York, 2002; p 493. (b) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566 and refs cited therein. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (d) Takahashi, S.; Kuroyama, K.; Sonogashira, K. Hagihara, N. Synthesis 1980, 627. (e) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467. (f) Dieck, H. A.; Heck, F. R. J. Organomet. Chem. 1975, 93, 259. (g) Cassar, L. J. Organomet. Chem. 1975, 93, 253.
10. For selected reviews and papers on the Sonogashira alkynylation and the Heck alkynylation, see: (a) Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Eds.; Wiley-Interscience: New York, 2002; p 493. (b) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566 and refs cited therein. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (d) Takahashi, S.; Kuroyama, K.; Sonogashira, K. Hagihara, N. Synthesis 1980, 627. (e) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467. (f) Dieck, H. A.; Heck, F. R. J. Organomet. Chem. 1975, 93, 259. (g) Cassar, L. J. Organomet. Chem. 1975, 93, 253.
11. For selected papers and reviews of the Pd-catalyzed coupling reaction of alkynylmetal compounds with aryl halides, see the following. For Zn: (a) Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. (b) Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219. (c) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957. (d) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A.; Bull. Chem. Soc. Jpn. 1990, 63, 2124. For Sn: (e) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403. (f) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138. For B: (h) Oh, C. H.; Jung, S. H.; Tetrahedron Lett. 2000, 41, 8513. (i) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165. For Al: (j) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340. For Si: (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Morío, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
12. For selected papers and reviews of the Pd-catalyzed coupling reaction of alkynylmetal compounds with aryl halides, see the following. For Zn: (a) Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. (b) Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219. (c) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957. (d) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A.; Bull. Chem. Soc. Jpn. 1990, 63, 2124. For Sn: (e) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403. (f) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138. For B: (h) Oh, C. H.; Jung, S. H.; Tetrahedron Lett. 2000, 41, 8513. (i) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165. For Al: (j) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340. For Si: (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Morío, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
13. For selected papers and reviews of the Pd-catalyzed coupling reaction of alkynylmetal compounds with aryl halides, see the following. For Zn: (a) Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. (b) Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219. (c) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957. (d) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A.; Bull. Chem. Soc. Jpn. 1990, 63, 2124. For Sn: (e) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403. (f) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138. For B: (h) Oh, C. H.; Jung, S. H.; Tetrahedron Lett. 2000, 41, 8513. (i) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165. For Al: (j) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340. For Si: (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Morío, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
14. For selected papers and reviews of the Pd-catalyzed coupling reaction of alkynylmetal compounds with aryl halides, see the following. For Zn: (a) Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. (b) Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219. (c) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957. (d) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A.; Bull. Chem. Soc. Jpn. 1990, 63, 2124. For Sn: (e) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403. (f) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138. For B: (h) Oh, C. H.; Jung, S. H.; Tetrahedron Lett. 2000, 41, 8513. (i) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165. For Al: (j) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340. For Si: (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Morío, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
15. For selected papers and reviews of the Pd-catalyzed coupling reaction of alkynylmetal compounds with aryl halides, see the following. For Zn: (a) Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. (b) Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219. (c) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957. (d) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A.; Bull. Chem. Soc. Jpn. 1990, 63, 2124. For Sn: (e) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403. (f) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138. For B: (h) Oh, C. H.; Jung, S. H.; Tetrahedron Lett. 2000, 41, 8513. (i) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165. For Al: (j) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340. For Si: (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Morío, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
16. For selected papers and reviews of the Pd-catalyzed coupling reaction of alkynylmetal compounds with aryl halides, see the following. For Zn: (a) Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. (b) Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219. (c) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957. (d) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A.; Bull. Chem. Soc. Jpn. 1990, 63, 2124. For Sn: (e) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403. (f) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138. For B: (h) Oh, C. H.; Jung, S. H.; Tetrahedron Lett. 2000, 41, 8513. (i) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165. For Al: (j) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340. For Si: (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Morío, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
17. For selected papers and reviews of the Pd-catalyzed coupling reaction of alkynylmetal compounds with aryl halides, see the following. For Zn: (a) Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. (b) Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219. (c) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957. (d) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A.; Bull. Chem. Soc. Jpn. 1990, 63, 2124. For Sn: (e) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403. (f) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138. For B: (h) Oh, C. H.; Jung, S. H.; Tetrahedron Lett. 2000, 41, 8513. (i) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165. For Al: (j) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340. For Si: (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Morío, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
18. For selected papers and reviews of the Pd-catalyzed coupling reaction of alkynylmetal compounds with aryl halides, see the following. For Zn: (a) Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. (b) Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219. (c) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957. (d) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A.; Bull. Chem. Soc. Jpn. 1990, 63, 2124. For Sn: (e) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403. (f) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138. For B: (h) Oh, C. H.; Jung, S. H.; Tetrahedron Lett. 2000, 41, 8513. (i) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165. For Al: (j) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340. For Si: (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Morío, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
19. For selected papers and reviews of the Pd-catalyzed coupling reaction of alkynylmetal compounds with aryl halides, see the following. For Zn: (a) Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. (b) Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219. (c) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957. (d) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A.; Bull. Chem. Soc. Jpn. 1990, 63, 2124. For Sn: (e) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403. (f) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138. For B: (h) Oh, C. H.; Jung, S. H.; Tetrahedron Lett. 2000, 41, 8513. (i) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165. For Al: (j) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340. For Si: (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Morío, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
20. For selected papers and reviews of the Pd-catalyzed coupling reaction of alkynylmetal compounds with aryl halides, see the following. For Zn: (a) Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. (b) Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219. (c) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957. (d) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A.; Bull. Chem. Soc. Jpn. 1990, 63, 2124. For Sn: (e) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403. (f) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138. For B: (h) Oh, C. H.; Jung, S. H.; Tetrahedron Lett. 2000, 41, 8513. (i) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165. For Al: (j) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340. For Si: (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Morío, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
21. For selected papers and reviews of the Pd-catalyzed coupling reaction of alkynylmetal compounds with aryl halides, see the following. For Zn: (a) Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. (b) Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219. (c) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957. (d) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A.; Bull. Chem. Soc. Jpn. 1990, 63, 2124. For Sn: (e) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403. (f) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138. For B: (h) Oh, C. H.; Jung, S. H.; Tetrahedron Lett. 2000, 41, 8513. (i) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165. For Al: (j) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340. For Si: (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Morío, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
22. For selected papers and reviews of the Pd-catalyzed coupling reaction of alkynylmetal compounds with aryl halides, see the following. For Zn: (a) Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597. (b) Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219. (c) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957. (d) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A.; Bull. Chem. Soc. Jpn. 1990, 63, 2124. For Sn: (e) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403. (f) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193. (g) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138. For B: (h) Oh, C. H.; Jung, S. H.; Tetrahedron Lett. 2000, 41, 8513. (i) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165. For Al: (j) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287. (k) Negishi, E. Acc. Chem. Res. 1982, 15, 340. For Si: (l) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-I.; Morío, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
23. For selected recent advantages of the Sonogashira-type reaction, (a) see ref 2b. (b) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. (c) Méry, D.; Heuzé, K.; Astruc, S. Chem. Commun. 2003, 1934. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642. (f) Remmele, H.; Köllhofer, A.; Plenio, H. Organometallics 2003, 22, 4098. (g) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020. (h) Batey, R. A.; Shen, M.; Lough, A. Org. Lett. 2002, 4, 1411. (i) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
24. For selected recent advantages of the Sonogashira-type reaction, (a) see ref 2b. (b) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. (c) Méry, D.; Heuzé, K.; Astruc, S. Chem. Commun. 2003, 1934. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642. (f) Remmele, H.; Köllhofer, A.; Plenio, H. Organometallics 2003, 22, 4098. (g) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020. (h) Batey, R. A.; Shen, M.; Lough, A. Org. Lett. 2002, 4, 1411. (i) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
25. For selected recent advantages of the Sonogashira-type reaction, (a) see ref 2b. (b) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. (c) Méry, D.; Heuzé, K.; Astruc, S. Chem. Commun. 2003, 1934. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642. (f) Remmele, H.; Köllhofer, A.; Plenio, H. Organometallics 2003, 22, 4098. (g) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020. (h) Batey, R. A.; Shen, M.; Lough, A. Org. Lett. 2002, 4, 1411. (i) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
26. For selected recent advantages of the Sonogashira-type reaction, (a) see ref 2b. (b) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. (c) Méry, D.; Heuzé, K.; Astruc, S. Chem. Commun. 2003, 1934. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642. (f) Remmele, H.; Köllhofer, A.; Plenio, H. Organometallics 2003, 22, 4098. (g) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020. (h) Batey, R. A.; Shen, M.; Lough, A. Org. Lett. 2002, 4, 1411. (i) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
27. For selected recent advantages of the Sonogashira-type reaction, (a) see ref 2b. (b) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. (c) Méry, D.; Heuzé, K.; Astruc, S. Chem. Commun. 2003, 1934. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642. (f) Remmele, H.; Köllhofer, A.; Plenio, H. Organometallics 2003, 22, 4098. (g) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020. (h) Batey, R. A.; Shen, M.; Lough, A. Org. Lett. 2002, 4, 1411. (i) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
28. For selected recent advantages of the Sonogashira-type reaction, (a) see ref 2b. (b) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. (c) Méry, D.; Heuzé, K.; Astruc, S. Chem. Commun. 2003, 1934. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642. (f) Remmele, H.; Köllhofer, A.; Plenio, H. Organometallics 2003, 22, 4098. (g) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020. (h) Batey, R. A.; Shen, M.; Lough, A. Org. Lett. 2002, 4, 1411. (i) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
29. For selected recent advantages of the Sonogashira-type reaction, (a) see ref 2b. (b) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. (c) Méry, D.; Heuzé, K.; Astruc, S. Chem. Commun. 2003, 1934. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642. (f) Remmele, H.; Köllhofer, A.; Plenio, H. Organometallics 2003, 22, 4098. (g) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020. (h) Batey, R. A.; Shen, M.; Lough, A. Org. Lett. 2002, 4, 1411. (i) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
30. For selected recent advantages of the Sonogashira-type reaction, (a) see ref 2b. (b) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. (c) Méry, D.; Heuzé, K.; Astruc, S. Chem. Commun. 2003, 1934. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642. (f) Remmele, H.; Köllhofer, A.; Plenio, H. Organometallics 2003, 22, 4098. (g) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020. (h) Batey, R. A.; Shen, M.; Lough, A. Org. Lett. 2002, 4, 1411. (i) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
31. For selected recent advantages of the Sonogashira-type reaction, (a) see ref 2b. (b) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. (c) Méry, D.; Heuzé, K.; Astruc, S. Chem. Commun. 2003, 1934. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642. (f) Remmele, H.; Köllhofer, A.; Plenio, H. Organometallics 2003, 22, 4098. (g) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020. (h) Batey, R. A.; Shen, M.; Lough, A. Org. Lett. 2002, 4, 1411. (i) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
32. For selected recent advantages of the Sonogashira-type reaction, (a) see ref 2b. (b) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. (c) Méry, D.; Heuzé, K.; Astruc, S. Chem. Commun. 2003, 1934. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642. (f) Remmele, H.; Köllhofer, A.; Plenio, H. Organometallics 2003, 22, 4098. (g) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020. (h) Batey, R. A.; Shen, M.; Lough, A. Org. Lett. 2002, 4, 1411. (i) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
33. For selected recent advantages of the Sonogashira-type reaction, (a) see ref 2b. (b) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. (c) Méry, D.; Heuzé, K.; Astruc, S. Chem. Commun. 2003, 1934. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642. (f) Remmele, H.; Köllhofer, A.; Plenio, H. Organometallics 2003, 22, 4098. (g) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020. (h) Batey, R. A.; Shen, M.; Lough, A. Org. Lett. 2002, 4, 1411. (i) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
34. For selected recent advantages of the Sonogashira-type reaction, (a) see ref 2b. (b) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. (c) Méry, D.; Heuzé, K.; Astruc, S. Chem. Commun. 2003, 1934. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642. (f) Remmele, H.; Köllhofer, A.; Plenio, H. Organometallics 2003, 22, 4098. (g) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020. (h) Batey, R. A.; Shen, M.; Lough, A. Org. Lett. 2002, 4, 1411. (i) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818. (j) Alami, M.; Crousse, B.; Ferri, F. J. Organomet. Chem. 2001, 624, 114. (k) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (l) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
35. (a) Bandini, M.; Melchiorre, P.; Melloni, A.; Umani-Ronchi, A. Synlett 2002, 1110.
36. (b) Onishi, Y.; Ito, T.; Yasuda, M.; Baba, A. Eur. J. Org. Chem. 2002, 1578.
37. (c) Nagarajan, R.; Perumal, P. T. Tetrahedron 2002, 58, 1229.
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46. (a) Lee, P. H.; Lee, S. W.; Seomoon, D. Org. Lett. 2003, 5, 4963.
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50. (e) Lee, K.; Lee, J.; Lee, P. H. J. Org. Chem. 2002, 67, 8265.
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54. 3 as a cocatalyst in Pd-catalyzed cross-coupling reaction; see: Qian, M.; Huang, Z.; Negishi, E. Org. Lett. 2004, 6, 1531.
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58. With amines as the solvent, a reaction using pyrrolidine gave a similar result (72% under the same conditions in run 1, Table 1), although coupling reactions using other amines such as triethylamine and diethylamine did not proceed and the starting materials were recovered.
59. 2 were not effective for this reaction.
60. 3 showed a similar result. For example, the reaction using 2a was complete within 15 min and the yield of product 3aa was 98%.
61. 3 was carried out, the reaction time was prolonged (5 h) and the product yield of 3aa was decreased to 68%.
62. Intramolecular cycloaddition of 3cd did not proceed at all.
63. (a) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843.
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