Copper promoted C-N and C-O bond cross-coupling with phenyl and pyridylboronates

Tetrahedron Letters

Volumn 44, Issue 19, 2003, Pages 3863-3865

  Chan, Dominic M T ^a   Monaco, Kevin L ^a   Li, Renhua ^b   Bonne, Damien ^b   Clark, Charles G ^b   Lam, Patrick Y S ^b  

^a DUPONT COMPANY   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; BORONIC ACID DERIVATIVE; BOROXINE; CARBON; COPPER; ESTER DERIVATIVE; INDAZOLE DERIVATIVE; NITROGEN; OXYGEN; PHENYLBORONIC ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDYLBORONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CROSS LINKING; REACTION ANALYSIS;

EID: 0037420766     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00739-1     Document Type: Article

References (36)

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13. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
14. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
15. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
16. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
17. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
18. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
19. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
20. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
21. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
22. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
23. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
24. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
25. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
26. For application in N-arylation, see: (a) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982; (b) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (c) Collot, V.; Bovy, P. R.; Raulto, S. Tetrahedron Lett. 2000, 41, 9053-9057. For O-arylation, see: (d) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (g) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (h) Simon, J.; Salzbrunn, S.; Prakash, G. K. S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634. For S-arylation, see: (i) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022; (j) Savarin, C.; Srojl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312. For catalytic systems, see: (k) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236; (l) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418; (m) Antilla, J.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079; (n) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531; (o) Collman, J. P.; Zhong, M.; Zheng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
27. Lam P.Y.S., Deudon S., Kristin M.A., Li R., He M., DeShong P., Clark C.G. J. Am. Chem. Soc. 122:2000;7600-7601.
28. Lam P.Y.S., Deudon S., Hauptman E., Clark C.G. Tetrahedron Lett. 42:2001;2427-2429.
29. Lam P.Y.S., Vincent G., Bonne D., Clark C.G. Tetrahedron Lett. 43:2002;3091-3094.
30. Kang S.-K., Lee S.-H., Lee D. Synlett. 2000;1022-1024.
31. It should be noted that the parent phenyl system is probably one of the least effective arylating agents in our chemistry, see Refs. 1a and 4a. Most substituted systems give much more respectable yields.
32. 6-DMSO, the OH protons show up as singlet at δ 8.3 ppm.
33. Obtained commercially from Lancaster Synthesis Inc.
34. No cross-coupling occurs between 4-pyridylboronic acid and the ethyl ester of 3-methyl-5-pyrazole carboxylic acid. This pyrazole was previously shown to be a good substrate for N-arylation. We thank Dr. Yun-Long Li for this observation.
35. 3 in MeOH was added. The mixture was filtered through a layer of glass wool on Celite and purified by silica gel chromatography (ethyl acetate) to give 35 mg (54%) of 1-(3-pyridyl)-benzimidazole.
36. 3) theoretical: C, 73.83%; H, 4.656; N, 21.52; found: C, 73.49%; H, 4.78; N, 21.67.