A general strategy for organocatalytic activation of c-h bonds via photoredox catalysis: Direct arylation of benzylic ethers

Journal of the American Chemical Society

Volumn 136, Issue 2, 2014, Pages 626-629

  Qvortrup, Katrine ^a   Rankic, Danica A ^a   MacMillan, David W C ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; BENZYL ETHERS; BENZYLIC ETHERS; C-H FUNCTIONALIZATION; ORGANOCATALYSIS; ORGANOCATALYTIC; PHOTOREDOX CATALYSIS; REGIOISOMERS;

CATALYSIS; CATALYSTS; ETHERS; REACTION KINETICS;

AROMATIC COMPOUNDS;

CARBON; DIHYDROFURAN; FURAN DERIVATIVE; HYDROGEN; IRIDIUM; THIOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ORGANOCATALYSIS; PHOTOREDOX CATALYSIS;

BENZYL COMPOUNDS; CATALYSIS; ETHERS; FURANS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES;

EID: 84892765206     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja411596q     Document Type: Article

References (40)

1. Bergman, R. G. Nature 2007, 446, 391
2. Godula, K.; Sames, D. Science 2006, 312, 67
3. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507
4. Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069
5. McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114
6. For an overview of reduction potentials of amines, amides, and carbamates, see: Steckhan, E. In Organic Electrochemistry, 4th ed.; Henning, L.; Baizer, M., Eds.; Marcel Dekker Inc.: New York, 2001; p 570 and references therein.
7. Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press LLC: Boca Raton, FL, 2003.
8. Mayer, J. M. Acc. Chem. Res. 2011, 44, 36
9. Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363
10. Huynh, M. H. V.; Meyer, T. J. Chem. Rev. 2004, 107, 5004
11. Tyson, E. L.; Ament, M. S.; Yoon, T. P. J. Org. Chem. 2013, 78, 2046
12. DeForest, C. A.; Anseth, K. S. Angew. Chem., Int. Ed. 2012, 51, 1816
13. For some related examples on thiyl hydrogen atom abstraction catalysis in organic synthesis, see: Feray, L.; Kuznetsov, N.; Renaud, P. In Radicals in Organic Synthesis, Vol. 2; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; p 256 and references therein.
14. Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25
15. Dang, H.-S.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 1 1998, 67
16. Dang, H.-S.; Roberts, B. P. Tetrahedron Lett. 1999, 404, 8929
17. Bernardi, R.; Caronna, T.; Poggi, G.; Vittimberga, B. M. J. Heterocycl. Chem. 1994, 31, 903
18. Zeng, X.; Cai, J.; Gu, Y. Tetrahedron Lett. 1995, 36, 7275
19. Bernardi, R.; Caronna, T.; Dal Pio Luogo, D.; Morrocchi, S.; Poggi, G.; Vittimberga, B. M. J. Chem. Soc., Perkin Trans. 1 1996, 1593
20. Bernardi, R.; Caronna, T.; Morrocchi, S.; Ursini, M. J. Heterocycl. Chem. 1996, 33, 1137
21. Tsuji, M.; Higashiyama, K.; Yamauchi, T.; Kubo, H.; Ohmiya, S. Heterocycles 2001, 54, 1027
22. Pirnot, M. T.; Rankic, D. A.; Martin, D. B. C.; MacMillan, D. W. C. Science 2013, 339, 1593
23. Hoshikawa, T.; Inoue, M. Chem. Sci. 2013, 4, 3118
24. Ameen, D.; Snape, T. J. Med. Chem. Commun. 2013, 4, 893
25. Schmidt, F.; Stemmler, R. T.; Rudolph, J.; Bolm, C. Chem. Soc. Rev. 2006, 35, 454
26. Braun, M. Angew. Chem., Int. Ed. 2012, 51, 2550
27. Flamigni, L.; Barbieri, A.; Sabatini, C.; Ventura, B.; Barigelletti, F. Top. Curr. Chem. 2007, 281, 143
28. Mori, Y.; Sakaguchi, W.; Hayashi, H. J. Phys. Chem. A 2000, 104, 4896
29. Shaidarova, L. G.; Ziganshina, S.-A.; Budnikov, G. K. J. Anal. Chem. 2003, 58, 640
30. Tarantino, K. T.; Liu, P.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 10022
31. Escoubet, S.; Gastaldi, G.; Vanthuyne, N.; Gil, G.; Siri, D.; Bertrand, M. J. Org. Chem. 2006, 71, 7288
32. Ochiai, M.; Yamane, S.; Hoque, M. M.; Saito, M.; Miyamoto, K. Chem. Commun. 2012, 48, 5280
33. Nakanishi, K. Natural Products Chemistry; Kodansha Ltd., Academic: New York, 1974.
34. Meyers, A. I. Heterocycles in Organic Synthesis; John Wiley & Sons: New York, 1974.
35. Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic: New York, 1982; Vol. 30, p 167.
36. Dean, F. M.; Sargent, M. V. In Comprehensive Heterocyclic Chemistry; Bird, C. W.; Cheeseman, G. W. H., Eds.; Pergamon: New York, 1984; Vol. 4, Part 3, p 531.
37. Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21
38. Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529
39. Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371
40. Schmidt, B. Chem. Commun. 2003, 1656