Activation of C-H bonds via the merger of photoredox and organocatalysis: A coupling of benzylic ethers with schiff bases

Journal of the American Chemical Society

Volumn 136, Issue 49, 2014, Pages 16986-16989

  Hager, Dominik ^a   Macmillan, David W C ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CHEMICAL ACTIVATION; FUNCTIONAL GROUPS; REACTION KINETICS;

ALDIMINES; BENZYLIC ETHERS; C-H ACTIVATION; C-H BOND; MECHANISTIC STUDIES; ORGANOCATALYSIS; RADICAL-RADICAL COUPLING; SCHIFF BASIS;

ETHERS;

ANION; BENZILIC ACID; ETHER DERIVATIVE; HYDROGEN; IRIDIUM; SCHIFF BASE; THIOL DERIVATIVE; BENZYL DERIVATIVE; IMINE; ORGANOMETALLIC COMPOUND;

ARTICLE; COVALENT BOND; ELECTRON TRANSPORT; ELECTROPHILICITY; IRRADIATION; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; PHOTOCATALYSIS; REACTION ANALYSIS; REACTION OPTIMIZATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; PHOTOCHEMISTRY; SYNTHESIS;

BENZYL COMPOUNDS; CATALYSIS; ETHERS; IMINES; IRIDIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES; SCHIFF BASES; SULFHYDRYL COMPOUNDS;

EID: 84918494493     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5102695     Document Type: Article

References (36)

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. Qvortrup, K.; Rankic, D. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 626
5. Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363
6. Huynh, M. H. V.; Meyer, T. J. Chem. Rev. 2007, 107, 5004
7. Warren, J. J.; Tronic, T. A.; Mayer, J. M. Chem. Rev. 2010, 110, 6961
8. Tyson, E. L.; Ament, M. S.; Yoon, T. P. J. Org. Chem. 2013, 78, 2046
9. Nguyen, T. M.; Manohar, N.; Nicewicz, D. A. Angew. Chem., Int. Ed. 2014, 53, 6198
10. DeForest, C. A.; Anseth, K. S. Angew. Chem., Int. Ed. 2012, 51, 1816
11. For some related examples on thiyl mediated hydrogen atom abstraction catalysis in organic synthesis, see: Feray, L.; Kuznetsov, N.; Renaud, P.; Sibi, M. P. In Radicals in Organic Synthesis, Vol. 2; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; p 256.
12. Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press LLC: Boca Raton, FL, 2003.
13. Mayer, J. M. Acc. Chem. Res. 2011, 44, 36
14. Arrasate, S.; Lete, E.; Sotomayor, N. Tetrahedron: Asymmetry 2002, 13, 311
15. Bergmeier, S. C. Tetrahedron 2000, 56, 2561
16. Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969
17. Cho, G. Y.; Ko, S. Y. J. Org. Chem. 1999, 64, 8745
18. Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25
19. Dang, H.-S.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 1 1998, 67
20. Dang, H.-S.; Roberts, B. P. Tetrahedron Lett. 1999, 404, 8929
21. Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77
22. Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875
23. McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114
24. Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224
25. Rono, L. J.; Yayla, H. G.; Wang, D. Y.; Armstrong, M. F.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 17735
26. Slinker, J. D.; Gorodetsky, A. A.; Lowry, M. S.; Wang, J.; Parker, S.; Rohl, R.; Bernhard, S.; Malliaras, G. G. J. Am. Chem. Soc. 2004, 126, 2763
27. Shaidarova, L. G.; Ziganshina, S.-A.; Budnikov, G. K. J. Anal. Chem. 2003, 58, 640
28. Root, D. K.; Smith, W. H. J. Electrochem. Soc. 1982, 129, 1231
29. Ochiai, M.; Yamane, S.; Hoque, M. M.; Saito, M.; Miyamoto, K. Chem. Commun. 2012, 48, 5280
30. Escoubet, S.; Gastaldi, G.; Vanthuyne, N.; Gil, G.; Siri, D.; Bertrand, M. P. J. Org. Chem. 2006, 71, 7288
31. Studer, A. Chem.-Eur. J. 2001, 7, 1159
32. Studer, A. Chem. Soc. Rev. 2004, 33, 267
33. Fischer, H. J. Am. Chem. Soc. 1986, 108, 3925
34. Rüegge, D.; Fischer, H. Int. J. Chem. Kinet. 1989, 21, 703
35. Kothe, T.; Marque, S.; Martschke, R.; Popov, M.; Fischer, H. J. Chem. Soc., Perkin Trans. 2 1998, 1553
36. Nguyen, J. D.; Reiß, B.; Dai, C.; Stephenson, C. R. J. Chem. Commun. 2013, 49, 4352