Photoredox activation for the direct β-arylation of ketones and aldehydes

Science

Volumn 340, Issue 6127, 2013, Pages 1593-1596

  Pirnot, Michael T ^a   Rankic, Danica A ^a   Martin, David B C ^a   MacMillan, David W C ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETONE;

ALDEHYDE; CATALYSIS; KETONE; PHOTOCHEMISTRY; REDOX CONDITIONS;

ARTICLE; ARYLATION; BETA ARYLATION; CHEMICAL REACTION; ENANTIOSELECTIVITY; PHOTOCATALYSIS; PHOTOREDOX CATALYSIS; PRIORITY JOURNAL; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY;

ALDEHYDES; CATALYSIS; KETONES; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES;

MLCS; MLOWN;

EID: 84875546445     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1232993     Document Type: Article

References (25)

1. D. A. Evans, G. Helmchen, M. Rüping, Asymmetric Synthesis - The Essentials (Wiley-VCH, Weinheim, Germany, 2006).
2. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 107, 5471 (2007).
3. A one-pot two-step oxidation, iminium-catalyzed β-functionalization process has been reported (4).
4. S.-L. Zhang et al., Nat. Commun. 2, 211 (2011).
5. R. Itooka, Y. Iguchi, N. Miyaura, J. Org. Chem. 68, 6000 (2003).
6. F. López, S. R. Harutyunyan, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 126, 12784 (2004).
7. N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 124, 7894 (2002).
8. A high-energy light promoted example of β-functionalization with preformed ketone enamines has been reported (9).
9. M. Kawanisi, K. Kamogawa, T. Okada, H. Nozaki, Tetrahedron 24, 6557 (1968).
10. M. Wasa, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 131, 9886 (2009).
11. A. Renaudat, L. Jean-Gerard, R. Jazzar, C. E. Kefalidis, E. Clot, O. Baudoin, Angew. Chem. Int. Ed. 49, 7261 (2010).
12. Y. Ano, M. Tobisu, N. Chatani, J. Am. Chem. Soc. 133, 12984 (2011).
13. M. V. Leskinen, K.-T. Yip, A. Valkonen, P. M. Pihko, J. Am. Chem. Soc. 134, 5750 (2012).
14. D. A. Nicewicz, D. W. C. MacMillan, Science 322, 77 (2008).
15. M. A. Ischay, M. E. Anzovino, J. Du, T. P. Yoon, J. Am. Chem. Soc. 130, 12886 (2008).
16. J. M. R. Narayanam, J. W. Tucker, C. R. J. Stephenson, J. Am. Chem. Soc. Collect. Czech. Chem. Commun. 76, 859 (2011).
17. A. McNally, C. K. Prier, D. W. C. MacMillan, Science 334, 1114 (2011).
18. L. Flamigni, A. Barbieri, C. Sabatini, B. Ventura, F. Barigelletti, Top. Curr. Chem. 281, 143 (2007).
19. I. M. Dixon et al., Chem. Soc. Rev. 29, 385 (2000).
20. Y. Mori, W. Sakaguchi, H. Hayashi, J. Phys. Chem. A 104, 4896 (2000).
21. V. P. Renaud, S. Schubert, Angew. Chem. 102, 416 (1990).
22. D. Mangion, D. R. Arnold, Acc. Chem. Res. 35, 297 (2002).
23. All calculations were performed with Gaussian 09 (25).
24. M. J. Frisch et al., Gaussian 09, Rev. B.01 (Gaussian Inc., Wallingford, CT, 2010).
25. See supplementary materials on Science Online.