Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids: Two distinct C-H activation pathways

Journal of the American Chemical Society

Volumn 128, Issue 39, 2006, Pages 12634-12635

  Chen, Xiao ^a   Goodhue, Charles E ^a   Yu, Jin Quan ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE; BORONIC ACID DERIVATIVE; CARBON; HYDROGEN; METHYLBOROXINE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL BINDING; METAL BINDING; METHYLATION; REGULATORY MECHANISM; SUZUKI REACTION;

EID: 33749509027     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0646747     Document Type: Article

References (34)

1. For reviews, see: (a) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
2. (b) Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005; Vols. 1 and 2.
3. (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
4. (b) Oi, S.; Fukita, S.; Inoue, Y. Chem. Commun. 1998, 2439.
5. (c) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1999, 121, 6616.
6. (d) Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
7. (e) Lim, Y. G.; Ahn, J.-A.; Jun, C.-H. Org. Lett. 2004, 6, 4687.
8. (f) Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192.
9. (g) Ackermann, L.; Althammer, A.; Born, R. Angew. Chem., Int. Ed. 2006, 45, 2619.
10. 3 C-H bonds, see: Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 3672.
11. (a) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
12. (b) Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586.
13. (a) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
14. (b) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
15. (c) Shabashov, D.; Daugulis, O. Org. Lett. 2005, 7, 3657.
16. (d) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
17. (e) Reddy, B. V.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391.
18. (a) Dyker, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 103.
19. (b) Catellani, M.; Frignani, F.; Rangoni, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 119.
20. (c) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506.
21. (d) Campeau, L. C.; Parisien, M.; Leblanc, M.; Fagnou, K. J. Am. Chem. Soc. 2004, 126, 9186.
22. (e) Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148.
23. (f) Dong, C.-G.; Hu, Q.-S. Angew. Chem., Int. Ed. 2006, 45, 2289.
24. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
25. Chen, X.; Li, J.-J.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 78.
26. Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662.
27. 3 C-H bonds in a single substrate with a vinylboronic acid, see: Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856.
28. (a) Lei, A.; Zhang, X. Org. Lett. 2002, 4, 2285.
29. (b) Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359.
30. 2O, see: Uenishi, Y.; Beau, J.-M.; Armstrong, R. W.; Kishi, Y. J. Am. Chem. Soc: 1987, 109, 4756.
31. 2 as an oxidant under the conditions indicated in Table 1.
32. 2 and boronic acids, see: Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
33. 11 with oxygen atom in a B-O bond, see: (a) Sumimoto, M.; Iwane, N.; Takahama, T.; Sakaki, S. J. Am. Chem. Soc. 2004, 126, 10457.
34. (b) McKinley, N. F.; O'Shea, D. F. J. Org. Chem. 2004, 69, 5087.