Visible-light-induced chemoselective deboronative alkynylation under biomolecule-compatible conditions

Journal of the American Chemical Society

Volumn 136, Issue 6, 2014, Pages 2280-2283

  Huang, Hanchu ^a   Zhang, Guojin ^a   Gong, Li ^a   Zhang, Shuaiyan ^a   Chen, Yiyun ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNES; BORON COMPOUNDS; CATALYSIS; GLUTAMIC ACID; LIGHT; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 84894179103     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja413208y     Document Type: Article

References (44)

1. Shenvi, R. A.; O'Malley, D. P.; Baran, P. S. Acc. Chem. Res. 2009, 42, 530
2. Afagh, N. A.; Yudin, A. K. Angew. Chem., Int. Ed. 2010, 49, 262
3. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
4. Sletten, E. M.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2009, 48, 6974
5. Rowlands, G. J. Tetrahedron 2009, 65, 8603
6. Li, C.-J. Chem. Rev. 2005, 105, 3095
7. Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886
8. Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77
9. Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756
10. Yoon, T. P.; Ischay, M. A.; Du, J. N. Nature Chem. 2010, 2, 527
11. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322
12. Fancy, D. A.; Kodadek, T. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 6020
13. Sato, S.; Nakamura, H. Angew. Chem., Int. Ed. 2013, 52, 8681
14. Chen, Y.; Kamlet, A. S.; Steinman, J. B.; Liu, D. R. Nature Chem. 2011, 3, 146
15. Sadhu, K. K.; Eierhoff, T.; Römer, W.; Winssinger, N. J. Am. Chem. Soc. 2012, 134, 20013
16. Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2 ed.; Wiley-VCH: Weinheim, Germany, 2011.
17. Fujiwara, Y.; Domingo, V.; Seiple, I. B.; Gianatassio, R.; Del Bel, M.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 3292
18. Liwosz, T. W.; Chemler, S. R. Org. Lett. 2013, 15, 3034
19. Sorin, G.; Mallorquin, R. M.; Contie, Y.; Baralle, A.; Malacria, M.; Goddard, J. P.; Fensterbank, L. Angew. Chem., Int. Ed. 2010, 49, 8721
20. Molander, G. A.; Colombel, V.; Braz, V. A. Org. Lett. 2011, 13, 1852
21. Neufeldt, S. R.; Seigerman, C. K.; Sanford, M. S. Org. Lett. 2013, 15, 2302
22. Tobisu, M.; Koh, K.; Furukawa, T.; Chatani, N. Angew. Chem., Int. Ed. 2012, 51, 11363
23. Yasu, Y.; Koike, T.; Akita, M. Adv. Synth. Catal. 2012, 354, 3414
24. Miyazawa, K.; Yasu, Y.; Koike, T.; Akita, M. Chem. Commun. 2013, 49, 7249
25. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128
26. Gong, J. C.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486
27. Back, T. G. Tetrahedron 2001, 57, 5263
28. Schaffner, A. P.; Darmency, V.; Renaud, P. Angew. Chem., Int. Ed. 2006, 45, 5847
29. Brand, J. P.; Waser, J. Chem. Soc. Rev. 2012, 41, 4165
30. Liu, X. S.; Wang, Z. T.; Cheng, X. M.; Li, C. Z. J. Am. Chem. Soc. 2012, 134, 14330
31. Ochiai, M.; Masaki, Y.; Shiro, M. J. Org. Chem. 1991, 56, 5511
32. Zhdankin, V. V.; Kuehl, C. J.; Krasutsky, A. P.; Bolz, J. T.; Simonsen, A. J. J. Org. Chem. 1996, 61, 6547
33. Zhdankin, V. V. Curr. Org. Synth. 2005, 2, 121
34. Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123
35. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299
36. Vogler, T.; Studer, A. Synthesis-Stuttgart 2008, 1979
37. Xiang, J. S.; Fuchs, P. L. Tetrahedron Lett. 1996, 37, 5269
38. Ochiai, M.; Kunishima, M.; Nagao, Y.; Fuji, K.; Shiro, M.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 8281
39. Stang, P. J. Angew. Chem., Int. Ed. 1992, 31, 274
40. Frei, R.; Waser, J. J. Am. Chem. Soc. 2013, 135, 9620
41. Wallentin, C. J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. J. Am. Chem. Soc. 2012, 134, 8875
42. Espelt, L. R.; Wiensch, E. M.; Yoon, T. P. J. Org. Chem 2013, 78, 4107
43. Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P.; Vonzelewsky, A. Coordin. Chem. Rev. 1988, 84, 85
44. Collins, K. D.; Glorius, F. Nature Chem. 2013, 5, 597