Reduction of aryl halides by consecutive visible light-induced electron transfer processes

Science

Volumn 346, Issue 6210, 2014, Pages 725-728

  Ghosh, Indrajit ^a   Ghosh, Tamal ^a   Bardagi, Javier I ^a   König, Burkhard ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYLPYRROLE; ARYL HALIDE; BROMIDE; CARBONYL DERIVATIVE; CHLORIDE; DIMETHYL SULFOXIDE; FLUORESCENT DYE; HALIDE; HYDROGEN; N,N DIMETHYLFORMAMIDE; POTASSIUM; PYRROLE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG; CARBON;

ANION; CATALYSIS; CHEMICAL BONDING; ELECTRON; HALIDE; PHOTOCHEMISTRY; RADICAL; REACTION KINETICS; REDUCTION;

ABSORPTION SPECTROSCOPY; ALKYLATION; ARTICLE; ARYLATION; BLUE LIGHT; CATALYST; COVALENT BOND; CYCLIZATION; DEGRADATION; DISSOCIATION; ELECTRON TRANSPORT; EXCITATION; IRRADIATION; LIGHT; MASS FRAGMENTOGRAPHY; OXIDATION; PHOTOCATALYSIS; PHOTOOXIDATION; PHOTORECEPTOR; PHOTOSYNTHESIS; REACTION TIME; REDUCTION; SOLUBILITY; SUBSTITUTION REACTION; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; RADIATION RESPONSE;

CARBON; CATALYSIS; CHLORIDES; ELECTRON TRANSPORT; HYDROGEN; LIGHT; OXIDATION-REDUCTION; PHOTOSYNTHESIS;

EID: 84910052051     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1258232     Document Type: Article

References (35)

1. J. J. Concepcion, R. L. House, J. M. Papanikolas, T. J. Meyer, Proc. Natl. Acad. Sci. U.S.A. 109, 15560-15564 (2012).
2. D. M. Schultz, T. P. Yoon, Science 343, 1239176 (2014).
3. C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 113, 5322-5363 (2013).
4. J. Xuan, W. J. Xiao, Angew. Chem. Int. Ed. 51, 6828-6838 (2012).
5. F. Tepl?, Collect. Czech. Chem. Commun. 76, 859-917 (2011).
6. D. P. Hari, P. Schroll, B. Koenig, J. Am. Chem. Soc. 134, 2958-2961 (2012).
7. D. Ravelli, D. Dondi, M. Fagnoni, A. Albini, Chem. Soc. Rev. 38, 1999-2011 (2009).
8. D. P. Hari, B. Koenig, Angew. Chem. Int. Ed. 52, 4734-4743 (2013).
9. J. D. Nguyen, E. M. D'Amato, J. M. R. Narayanam, C. R. J. Stephenson, Nat. Chem. 4, 854-859 (2012).
10. D. P. Hari, T. Hering, B. Koenig, Angew. Chem. Int. Ed. 53, 725 (2014).
11. Y. X. Liu et al., Synlett 24, 507-513 (2013).
12. H. Kim, C. Lee, Angew. Chem. Int. Ed. 51, 12303-12306 (2012).
13. The excited state redox potential of fac-Ir(ppy)3 is estimated to be -1.73 versus SCE (9). Some metal complexes with even stronger reducing power in the excited state have been reported but have not been applied to photoredox catalysis (14).
14. S. B. Harkins, J. C. Peters, J. Am. Chem. Soc. 127, 2030-2031 (2005).
15. The Rehm-Weller equation estimates the reduction potential of a photoredox catalyst in its excited state from the groundstate redox potential and the E 0-0 transition energy (28).
16. For a recent example of two-step photoexcitation (Z scheme) of heterogeneous semiconductor in water splitting, see (24).
17. M. T. Pirnot, D. A. Rankic, D. B. C. Martin, D. W. C. MacMillan, Science 339, 1593-1596 (2013).
18. L. Furst, B. S. Matsuura, J. M. R. Narayanam, J. W. Tucker, C. R. J. Stephenson, Org. Lett. 12, 3104-3107 (2010).
19. J. M. R. Narayanam, J. W. Tucker, C. R. J. Stephenson, J. Am. Chem. Soc. 131, 8756-8757 (2009).
20. D. A. Nicewicz, D. W. C. MacMillan, Science 322, 77-80 (2008).
21. E. Cahard et al., Angew. Chem. Int. Ed. 51, 3673-3676 (2012).
22. C. Costentin, M. Robert, J. M. Savéant, J. Am. Chem. Soc. 126, 16051-16057 (2004).
23. L. Pause, M. Robert, J. M. Saveant, J. Am. Chem. Soc. 121, 7158-7159 (1999).
24. Y. Sasaki, H. Kato, A. Kudo, J. Am. Chem. Soc. 135, 5441-5449 (2013).
25. F. Würthner, Chem. Commun. 2004 (14), 1564-1579 (2004).
26. D. Gosztola, M. P. Niemczyk, W. Svec, A. S. Lukas, M. R. Wasielewski, J. Phys. Chem. A 104, 6545-6551 (2000).
27. M. J. Tauber, R. F. Kelley, J. M. Giaimo, B. Rybtchinski, M. R. Wasielewski, J. Am. Chem. Soc. 128, 1782-1783 (2006).
28. D. Rehm, A. Weller, Isr. J. Chem. 8, 259-271 (1970).
29. C. Ramanan, A. L. Smeigh, J. E. Anthony, T. J. Marks, M. R. Wasielewski, J. Am. Chem. Soc. 134, 386-397 (2012).
30. M. E. Budén, J. F. Guastavino, R. A. Rossi, Org. Lett. 15, 1174-1177 (2013).
31. Y. Cheng, X. Gu, P. Li, Org. Lett. 15, 2664-2667 (2013).
32. R. A. Rossi, A. B. Pierini, A. B. Peñéñory, Chem. Rev. 103, 71-168 (2003).
33. Z. Chami, M. Gareil, J. Pinson, J. M. Saveant, A. Thiebault, J. Org. Chem. 56, 586-595 (1991).
34. M. Newcomb, in Encyclopedia of Radicals in Chemistry, Biology and Materials, C. S. Chatgilialoglu, A. Studer, Eds. (Wiley, Chichester, UK, 2012)pp. 107-124.
35. E. Shirman et al., J. Phys. Chem. B112, 8855-8858 (2008).