A new entry in catalytic alkynylation of aldehydes and ketones: Dual activation of soft nucleophiles and hard electrophiles by an indium(III) catalyst

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1363-1366

  Takita, Ryo ^a   Fukuta, Yuhei ^a   Tsuji, Riichiro ^a   Ohshima, Takashi ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYNE; CARBONYL DERIVATIVE; INDIUM; KETONE;

ALKYNYLATION; ARTICLE; CATALYSIS; CATALYST; INFRARED RADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 17444379383     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050069h     Document Type: Article

References (60)

1. For a recent review, see: Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2004, 4095.
2. (a) For a review, see: Pu, L. Tetrahedron 2003, 59, 9873. See also ref 1.
3. For recent representative examples, see: (b) Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417. (c) Li, Z.-B.; Pu, L. Org. Lett. 2004, 6, 1065. (d) Xu, Z.; Chen, C.; Xu, J.; Miao, M.; Yan, W.; Wang, R. Org. Lett. 2004, 6, 1193. (e) Dahmen, S. Org. Lett. 2004, 6, 2113. (f) Liu, L.; Pu, L. Tetrahedron 2004, 60, 7427. (g) Kang, Y.-F.; Liu, L.; Wang, R.; Yan, W.-J.; Zhou, Y.-F. Tetrahedron: Asymmetry 2004, 15, 3155. For examples of alkynylation of ketones, see: (h) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895. (i) Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057. (j) Saito, B.; Katsuki, T. Synlett 2004, 1557. (k) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448. (l) Zhou, Y.; Wang, R.; Xu, Z.; Yan, W.; Liu, L.; Kang, Y.; Han, Z. Org. Lett. 2004, 6, 4147. (m) Liu, L.; Wang, R.; Kang, Y.-F.; Chen, C.; Xu, Z.-Q.; Zhou, Y.-F.; Ni, M.; Cai, H.-Q.; Gong, M.-Z. J. Org. Chem. 2005, 70, 1084.
4. For recent representative examples, see: (b) Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417. (c) Li, Z.-B.; Pu, L. Org. Lett. 2004, 6, 1065. (d) Xu, Z.; Chen, C.; Xu, J.; Miao, M.; Yan, W.; Wang, R. Org. Lett. 2004, 6, 1193. (e) Dahmen, S. Org. Lett. 2004, 6, 2113. (f) Liu, L.; Pu, L. Tetrahedron 2004, 60, 7427. (g) Kang, Y.-F.; Liu, L.; Wang, R.; Yan, W.-J.; Zhou, Y.-F. Tetrahedron: Asymmetry 2004, 15, 3155. For examples of alkynylation of ketones, see: (h) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895. (i) Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057. (j) Saito, B.; Katsuki, T. Synlett 2004, 1557. (k) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448. (l) Zhou, Y.; Wang, R.; Xu, Z.; Yan, W.; Liu, L.; Kang, Y.; Han, Z. Org. Lett. 2004, 6, 4147. (m) Liu, L.; Wang, R.; Kang, Y.-F.; Chen, C.; Xu, Z.-Q.; Zhou, Y.-F.; Ni, M.; Cai, H.-Q.; Gong, M.-Z. J. Org. Chem. 2005, 70, 1084.
5. For recent representative examples, see: (b) Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417. (c) Li, Z.-B.; Pu, L. Org. Lett. 2004, 6, 1065. (d) Xu, Z.; Chen, C.; Xu, J.; Miao, M.; Yan, W.; Wang, R. Org. Lett. 2004, 6, 1193. (e) Dahmen, S. Org. Lett. 2004, 6, 2113. (f) Liu, L.; Pu, L. Tetrahedron 2004, 60, 7427. (g) Kang, Y.-F.; Liu, L.; Wang, R.; Yan, W.-J.; Zhou, Y.-F. Tetrahedron: Asymmetry 2004, 15, 3155. For examples of alkynylation of ketones, see: (h) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895. (i) Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057. (j) Saito, B.; Katsuki, T. Synlett 2004, 1557. (k) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448. (l) Zhou, Y.; Wang, R.; Xu, Z.; Yan, W.; Liu, L.; Kang, Y.; Han, Z. Org. Lett. 2004, 6, 4147. (m) Liu, L.; Wang, R.; Kang, Y.-F.; Chen, C.; Xu, Z.-Q.; Zhou, Y.-F.; Ni, M.; Cai, H.-Q.; Gong, M.-Z. J. Org. Chem. 2005, 70, 1084.
6. For recent representative examples, see: (b) Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417. (c) Li, Z.-B.; Pu, L. Org. Lett. 2004, 6, 1065. (d) Xu, Z.; Chen, C.; Xu, J.; Miao, M.; Yan, W.; Wang, R. Org. Lett. 2004, 6, 1193. (e) Dahmen, S. Org. Lett. 2004, 6, 2113. (f) Liu, L.; Pu, L. Tetrahedron 2004, 60, 7427. (g) Kang, Y.-F.; Liu, L.; Wang, R.; Yan, W.-J.; Zhou, Y.-F. Tetrahedron: Asymmetry 2004, 15, 3155. For examples of alkynylation of ketones, see: (h) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895. (i) Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057. (j) Saito, B.; Katsuki, T. Synlett 2004, 1557. (k) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448. (l) Zhou, Y.; Wang, R.; Xu, Z.; Yan, W.; Liu, L.; Kang, Y.; Han, Z. Org. Lett. 2004, 6, 4147. (m) Liu, L.; Wang, R.; Kang, Y.-F.; Chen, C.; Xu, Z.-Q.; Zhou, Y.-F.; Ni, M.; Cai, H.-Q.; Gong, M.-Z. J. Org. Chem. 2005, 70, 1084.
7. For recent representative examples, see: (b) Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417. (c) Li, Z.-B.; Pu, L. Org. Lett. 2004, 6, 1065. (d) Xu, Z.; Chen, C.; Xu, J.; Miao, M.; Yan, W.; Wang, R. Org. Lett. 2004, 6, 1193. (e) Dahmen, S. Org. Lett. 2004, 6, 2113. (f) Liu, L.; Pu, L. Tetrahedron 2004, 60, 7427. (g) Kang, Y.-F.; Liu, L.; Wang, R.; Yan, W.-J.; Zhou, Y.-F. Tetrahedron: Asymmetry 2004, 15, 3155. For examples of alkynylation of ketones, see: (h) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895. (i) Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057. (j) Saito, B.; Katsuki, T. Synlett 2004, 1557. (k) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448. (l) Zhou, Y.; Wang, R.; Xu, Z.; Yan, W.; Liu, L.; Kang, Y.; Han, Z. Org. Lett. 2004, 6, 4147. (m) Liu, L.; Wang, R.; Kang, Y.-F.; Chen, C.; Xu, Z.-Q.; Zhou, Y.-F.; Ni, M.; Cai, H.-Q.; Gong, M.-Z. J. Org. Chem. 2005, 70, 1084.
8. For recent representative examples, see: (b) Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417. (c) Li, Z.-B.; Pu, L. Org. Lett. 2004, 6, 1065. (d) Xu, Z.; Chen, C.; Xu, J.; Miao, M.; Yan, W.; Wang, R. Org. Lett. 2004, 6, 1193. (e) Dahmen, S. Org. Lett. 2004, 6, 2113. (f) Liu, L.; Pu, L. Tetrahedron 2004, 60, 7427. (g) Kang, Y.-F.; Liu, L.; Wang, R.; Yan, W.-J.; Zhou, Y.-F. Tetrahedron: Asymmetry 2004, 15, 3155. For examples of alkynylation of ketones, see: (h) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895. (i) Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057. (j) Saito, B.; Katsuki, T. Synlett 2004, 1557. (k) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448. (l) Zhou, Y.; Wang, R.; Xu, Z.; Yan, W.; Liu, L.; Kang, Y.; Han, Z. Org. Lett. 2004, 6, 4147. (m) Liu, L.; Wang, R.; Kang, Y.-F.; Chen, C.; Xu, Z.-Q.; Zhou, Y.-F.; Ni, M.; Cai, H.-Q.; Gong, M.-Z. J. Org. Chem. 2005, 70, 1084.
9. For recent representative examples, see: (b) Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417. (c) Li, Z.-B.; Pu, L. Org. Lett. 2004, 6, 1065. (d) Xu, Z.; Chen, C.; Xu, J.; Miao, M.; Yan, W.; Wang, R. Org. Lett. 2004, 6, 1193. (e) Dahmen, S. Org. Lett. 2004, 6, 2113. (f) Liu, L.; Pu, L. Tetrahedron 2004, 60, 7427. (g) Kang, Y.-F.; Liu, L.; Wang, R.; Yan, W.-J.; Zhou, Y.-F. Tetrahedron: Asymmetry 2004, 15, 3155. For examples of alkynylation of ketones, see: (h) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895. (i) Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057. (j) Saito, B.; Katsuki, T. Synlett 2004, 1557. (k) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448. (l) Zhou, Y.; Wang, R.; Xu, Z.; Yan, W.; Liu, L.; Kang, Y.; Han, Z. Org. Lett. 2004, 6, 4147. (m) Liu, L.; Wang, R.; Kang, Y.-F.; Chen, C.; Xu, Z.-Q.; Zhou, Y.-F.; Ni, M.; Cai, H.-Q.; Gong, M.-Z. J. Org. Chem. 2005, 70, 1084.
10. For recent representative examples, see: (b) Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417. (c) Li, Z.-B.; Pu, L. Org. Lett. 2004, 6, 1065. (d) Xu, Z.; Chen, C.; Xu, J.; Miao, M.; Yan, W.; Wang, R. Org. Lett. 2004, 6, 1193. (e) Dahmen, S. Org. Lett. 2004, 6, 2113. (f) Liu, L.; Pu, L. Tetrahedron 2004, 60, 7427. (g) Kang, Y.-F.; Liu, L.; Wang, R.; Yan, W.-J.; Zhou, Y.-F. Tetrahedron: Asymmetry 2004, 15, 3155. For examples of alkynylation of ketones, see: (h) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895. (i) Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057. (j) Saito, B.; Katsuki, T. Synlett 2004, 1557. (k) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448. (l) Zhou, Y.; Wang, R.; Xu, Z.; Yan, W.; Liu, L.; Kang, Y.; Han, Z. Org. Lett. 2004, 6, 4147. (m) Liu, L.; Wang, R.; Kang, Y.-F.; Chen, C.; Xu, Z.-Q.; Zhou, Y.-F.; Ni, M.; Cai, H.-Q.; Gong, M.-Z. J. Org. Chem. 2005, 70, 1084.
11. For recent representative examples, see: (b) Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417. (c) Li, Z.-B.; Pu, L. Org. Lett. 2004, 6, 1065. (d) Xu, Z.; Chen, C.; Xu, J.; Miao, M.; Yan, W.; Wang, R. Org. Lett. 2004, 6, 1193. (e) Dahmen, S. Org. Lett. 2004, 6, 2113. (f) Liu, L.; Pu, L. Tetrahedron 2004, 60, 7427. (g) Kang, Y.-F.; Liu, L.; Wang, R.; Yan, W.-J.; Zhou, Y.-F. Tetrahedron: Asymmetry 2004, 15, 3155. For examples of alkynylation of ketones, see: (h) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895. (i) Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057. (j) Saito, B.; Katsuki, T. Synlett 2004, 1557. (k) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448. (l) Zhou, Y.; Wang, R.; Xu, Z.; Yan, W.; Liu, L.; Kang, Y.; Han, Z. Org. Lett. 2004, 6, 4147. (m) Liu, L.; Wang, R.; Kang, Y.-F.; Chen, C.; Xu, Z.-Q.; Zhou, Y.-F.; Ni, M.; Cai, H.-Q.; Gong, M.-Z. J. Org. Chem. 2005, 70, 1084.
12. For recent representative examples, see: (b) Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417. (c) Li, Z.-B.; Pu, L. Org. Lett. 2004, 6, 1065. (d) Xu, Z.; Chen, C.; Xu, J.; Miao, M.; Yan, W.; Wang, R. Org. Lett. 2004, 6, 1193. (e) Dahmen, S. Org. Lett. 2004, 6, 2113. (f) Liu, L.; Pu, L. Tetrahedron 2004, 60, 7427. (g) Kang, Y.-F.; Liu, L.; Wang, R.; Yan, W.-J.; Zhou, Y.-F. Tetrahedron: Asymmetry 2004, 15, 3155. For examples of alkynylation of ketones, see: (h) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895. (i) Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057. (j) Saito, B.; Katsuki, T. Synlett 2004, 1557. (k) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448. (l) Zhou, Y.; Wang, R.; Xu, Z.; Yan, W.; Liu, L.; Kang, Y.; Han, Z. Org. Lett. 2004, 6, 4147. (m) Liu, L.; Wang, R.; Kang, Y.-F.; Chen, C.; Xu, Z.-Q.; Zhou, Y.-F.; Ni, M.; Cai, H.-Q.; Gong, M.-Z. J. Org. Chem. 2005, 70, 1084.
13. For recent representative examples, see: (b) Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417. (c) Li, Z.-B.; Pu, L. Org. Lett. 2004, 6, 1065. (d) Xu, Z.; Chen, C.; Xu, J.; Miao, M.; Yan, W.; Wang, R. Org. Lett. 2004, 6, 1193. (e) Dahmen, S. Org. Lett. 2004, 6, 2113. (f) Liu, L.; Pu, L. Tetrahedron 2004, 60, 7427. (g) Kang, Y.-F.; Liu, L.; Wang, R.; Yan, W.-J.; Zhou, Y.-F. Tetrahedron: Asymmetry 2004, 15, 3155. For examples of alkynylation of ketones, see: (h) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895. (i) Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057. (j) Saito, B.; Katsuki, T. Synlett 2004, 1557. (k) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448. (l) Zhou, Y.; Wang, R.; Xu, Z.; Yan, W.; Liu, L.; Kang, Y.; Han, Z. Org. Lett. 2004, 6, 4147. (m) Liu, L.; Wang, R.; Kang, Y.-F.; Chen, C.; Xu, Z.-Q.; Zhou, Y.-F.; Ni, M.; Cai, H.-Q.; Gong, M.-Z. J. Org. Chem. 2005, 70, 1084.
14. For recent representative examples, see: (b) Gao, G.; Xie, R.-G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5417. (c) Li, Z.-B.; Pu, L. Org. Lett. 2004, 6, 1065. (d) Xu, Z.; Chen, C.; Xu, J.; Miao, M.; Yan, W.; Wang, R. Org. Lett. 2004, 6, 1193. (e) Dahmen, S. Org. Lett. 2004, 6, 2113. (f) Liu, L.; Pu, L. Tetrahedron 2004, 60, 7427. (g) Kang, Y.-F.; Liu, L.; Wang, R.; Yan, W.-J.; Zhou, Y.-F. Tetrahedron: Asymmetry 2004, 15, 3155. For examples of alkynylation of ketones, see: (h) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895. (i) Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057. (j) Saito, B.; Katsuki, T. Synlett 2004, 1557. (k) Cozzi, P. G.; Alesi, S. Chem. Commun. 2004, 2448. (l) Zhou, Y.; Wang, R.; Xu, Z.; Yan, W.; Liu, L.; Kang, Y.; Han, Z. Org. Lett. 2004, 6, 4147. (m) Liu, L.; Wang, R.; Kang, Y.-F.; Chen, C.; Xu, Z.-Q.; Zhou, Y.-F.; Ni, M.; Cai, H.-Q.; Gong, M.-Z. J. Org. Chem. 2005, 70, 1084.
15. For reviews, see: (a) Alcaide, B.; Almendros, P. Eur. J. Org. Chem. 2002, 1595. (b) List, B. Tetrahedron 2002, 58, 5573.
16. For reviews, see: (a) Alcaide, B.; Almendros, P. Eur. J. Org. Chem. 2002, 1595. (b) List, B. Tetrahedron 2002, 58, 5573.
17. (a) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187.
18. (b) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989.
19. (c) Ma, J.-A.; Cahard, D. Angew. Chem., Int. Ed. 2004, 43, 4566.
20. Multimetallic Catalysts in Organic Synthesis; Shibasaki, M., Yamamoto, Y., Eds.; Wiley-VCH: Weinheim, 2004.
21. (a) Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806.
22. (b) Frantz, D. E.; Fässler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373
23. (c) Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687.
24. (d) Fässler, R.; Tomooka, C. S.; Frantz, D. E.; Carreira, E. M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5843.
25. See also: (e) Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 1999, 121, 11245.
26. 3: (e) Sakai, N.; Hirasawa, M.; Konakahara, T. Tetrahedron Lett. 2003, 44, 4171.
27. 3: (e) Sakai, N.; Hirasawa, M.; Konakahara, T. Tetrahedron Lett. 2003, 44, 4171.
28. 3: (e) Sakai, N.; Hirasawa, M.; Konakahara, T. Tetrahedron Lett. 2003, 44, 4171.
29. 3: (e) Sakai, N.; Hirasawa, M.; Konakahara, T. Tetrahedron Lett. 2003, 44, 4171.
30. 3: (e) Sakai, N.; Hirasawa, M.; Konakahara, T. Tetrahedron Lett. 2003, 44, 4171.
31. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
32. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
33. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
34. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
35. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
36. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
37. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
38. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
39. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
40. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
41. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
42. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
43. Although late transition metals such as Cu(I), Ag(I), and Au(I) are effective for the formation of metal acetylides in a similar way as Zn(II), they can be utilized for alkynylation of C=N compounds such as imines, but not for alkynylation of carbonyl coumpunds. For a review, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472. For representative examples of Cu, see: (b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638. (c) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535. (d) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763. (e) Black, D. A.; Arndtsen, B. A. Org. Lett. 2004, 6, 1107. Ag: (f) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42. Au: (h) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. Ir: (i) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319. (j) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497. Ru-Cu: (k) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268. For related works, see: (l) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810. (m) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
44. (a) Babler, J. H.; Liptak, V. P.; Phan, N. J. Org. Chem. 1996, 61, 416.
45. (b) Tzalis, D.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 1463.
46. (c) Miyamoto, H.; Yasaka, S.; Tanaka, K. Bull. Chem. Soc. Jpn. 2001, 74, 185.
47. (d) Ishikawa, T.; Mizuta, T.; Hagiwara, K.; Aikawa, T.; Kudo, T.; Saito, S. J. Org. Chem. 2003, 68, 3702.
48. (e) Imahori, T.; Hori, C.; Yamamoto, Y. Adv. Synth. Catal. 2004, 346, 1090.
49. 3 as a well-defined catalyst for alkynylation of aldehydes, although the chemical yields were moderate (27-62%, 12 entries) except for one entry (94%). They proposed that the C-H bond of alkyne is activated by the ruthenium catalyst and aldehyde is activated by the indium catalyst: Wei, C.; Li, C.-J. Green Chem. 2002, 4, 39.
50. (a) For a review, see: Chauhan, K. K.; Frost, C. G. J. Chem. Soc., Perkin Trans. I 2000, 3015.
51. For recent representative examples, see: (b) Lin, M.-J.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 13042. (c) Lu, J.; Ji, S.-J.; Teo, Y.-C.; Loh, T.-P. Org. Lett. 2005, 7, 159. (d) France, S.; Shah, M. H.; Weatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. J. Am. Chem. Soc. 2005, 127, 1206 and references therein.
52. For recent representative examples, see: (b) Lin, M.-J.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 13042. (c) Lu, J.; Ji, S.-J.; Teo, Y.-C.; Loh, T.-P. Org. Lett. 2005, 7, 159. (d) France, S.; Shah, M. H.; Weatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. J. Am. Chem. Soc. 2005, 127, 1206 and references therein.
53. For recent representative examples, see: (b) Lin, M.-J.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 13042. (c) Lu, J.; Ji, S.-J.; Teo, Y.-C.; Loh, T.-P. Org. Lett. 2005, 7, 159. (d) France, S.; Shah, M. H.; Weatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. J. Am. Chem. Soc. 2005, 127, 1206 and references therein.
54. For examples of catalytic activation of alkynes by In(III), see: (a) Tsuchimoto, T.; Maeda, T.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2000, 1573. (b) Tsuchimoto, T.; Hatanaka, K.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2003, 2454. (c) Nakamura, M.; Endo, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002. (d) Sakai, N.; Annaka, K.; Konakahara, T. Org. Lett. 2004, 6, 1527. See also ref 6e.
55. For examples of catalytic activation of alkynes by In(III), see: (a) Tsuchimoto, T.; Maeda, T.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2000, 1573. (b) Tsuchimoto, T.; Hatanaka, K.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2003, 2454. (c) Nakamura, M.; Endo, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002. (d) Sakai, N.; Annaka, K.; Konakahara, T. Org. Lett. 2004, 6, 1527. See also ref 6e.
56. For examples of catalytic activation of alkynes by In(III), see: (a) Tsuchimoto, T.; Maeda, T.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2000, 1573. (b) Tsuchimoto, T.; Hatanaka, K.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2003, 2454. (c) Nakamura, M.; Endo, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002. (d) Sakai, N.; Annaka, K.; Konakahara, T. Org. Lett. 2004, 6, 1527. See also ref 6e.
57. For examples of catalytic activation of alkynes by In(III), see: (a) Tsuchimoto, T.; Maeda, T.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2000, 1573. (b) Tsuchimoto, T.; Hatanaka, K.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2003, 2454. (c) Nakamura, M.; Endo, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002. (d) Sakai, N.; Annaka, K.; Konakahara, T. Org. Lett. 2004, 6, 1527. See also ref 6e.
58. See Supporting Information for details.
59. This signal disappeared when phenylacetylene was treated with EtMgBr in DME. See ref 5d.
60. 3, formation of indium diacetylide species was implied. For details, see Supporting Information.