Overturning established chemoselectivities: Selective reduction of arenes over malonates and cyanoacetates by photoactivated organic electron donors

Journal of the American Chemical Society

Volumn 135, Issue 30, 2013, Pages 10934-10937

  Doni, Eswararao ^a   Mondal, Bhaskar ^a   O'Sullivan, Steven ^a   Tuttle, Tell ^a   Murphy, John A ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL-SUBSTITUTED BENZENE; PHOTO ACTIVATIONS; PHOTO-ACTIVATED; REDUCING REAGENTS; SELECTIVE INTERACTION; SELECTIVE REDUCTION; STABILIZING INTERACTIONS; TRANSITION STATE;

METAL COMPLEXES; SUBSTRATES;

METALS;

ACETIC ACID DERIVATIVE; ALKALI METAL; BENZENE DERIVATIVE; CYANOACETIC ACID; ESTER DERIVATIVE; MALONIC ACID DERIVATIVE; METAL COMPLEX; NITRILE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DEBENZYLATION; DENSITY FUNCTIONAL THEORY; ELECTRON; ELECTRON TRANSPORT; ENANTIOSELECTIVITY; PHOTOACTIVATION; ULTRAVIOLET IRRADIATION;

EID: 84881067635     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4050168     Document Type: Article

References (49)

1. Bodnar, B. S.; Vogt, P. F. J. Org. Chem. 2009, 74, 2598
2. Bouveault, L.; Blanc, G. C. R. Hebd. Seances Acad. Sci. 1903, 136, 1676
3. Finley, K. T. Chem. Rev. 1964, 64, 5733
4. Rühlmann, K. Synthesis 1971, 236
5. Sautier, B.; Procter, D. J. Chimia 2012, 66, 399
6. Parmar, D.; Price, K.; Spain, M.; Matsubara, H.; Bradley, P. A.; Procter, D. J. J. Am. Chem. Soc. 2011, 133, 2418
7. Szostak, M.; Collins, K. D.; Fazakerley, N. J.; Spain, M.; Procter, D. M. Org. Biomol. Chem. 2012, 10, 5820
8. Lam, K.; Marko, I. E. Tetrahedron 2009, 65, 10930
9. Lam, K.; Marko, I. E. Org. Lett. 2009, 11, 2752
10. Organic Electrochemistry, 3 rd ed.; Baizer, M. M.; Lund, H., Eds.; Marcel Dekker: New York, 1991.
11. Portella, C.; Deshayes, H.; Pete, J. P.; Scholler, D. Tetrahedron 1984, 40, 3635
12. Mortensen, J.; Heinze, J. Angew. Chem., Int. Ed. Engl. 1984, 23, 84
13. Cram, D. J.; Steinberg, H. J. Am. Chem. Soc. 1951, 73, 5691
14. Birch, A. J. Q. Rev. Chem. Soc. 1950, 4, 69
15. Benkeser, R. A.; Belmonte, F. G.; Kang, J. J. Org. Chem. 1983, 48, 2796
16. Atherton, N. M.; Weissman, S. I. J. Am. Chem. Soc. 1961, 83, 1330
17. Carbery, D. R.; Donohoe, T. J. Chem. Commun. 2004, 722
18. Murphy, J. A.; Khan, T. A.; Zhou, S.-Z.; Thomson, D. W.; Mahesh, M. Angew. Chem., Int. Ed. 2005, 44, 1356
19. Murphy, J. A.; Zhou, S.-Z.; Thomson, D. W.; Schoenebeck, F.; Mohan, M.; Park, S. R.; Tuttle, T.; Berlouis, L. E. A. Angew. Chem., Int. Ed. 2007, 46, 5178
20. Murphy, J. A.; Garnier, J.; Park, S. R.; Schoenebeck, F.; Zhou, S.-Z.; Turner, A. T. Org. Lett. 2008, 10, 1227
21. Garnier, J.; Murphy, J. A.; Zhou, S. Z.; Turner, A. T. Synlett 2008, 2127
22. Cutulic, S. P. Y.; Murphy, J. A.; Farwaha, H.; Zhou, S. Z.; Chrystal, E. Synlett 2008, 2132
23. Murphy, J. A.; Schoenebeck, F.; Zhou, S.-Z.; Uenoyama, Y.; Miclo, Y.; Tuttle, T. J. Am. Chem. Soc. 2007, 129, 13368
24. Murphy, J. A.; Schoenebeck, F.; Findlay, N. J.; Thomson, D. W.; Zhou, S. Z.; Garnier, J. J. Am. Chem. Soc. 2009, 131, 6475
25. Sword, R.; Baldwin, L. A.; Murphy, J. A. Org. Biomol. Chem. 2011, 9, 3560
26. Cutulic, S. P. Y.; Findlay, N. J.; Zhou, S.-Z.; Chrystal, E. J. T.; Murphy, J. A. J. Org. Chem. 2009, 74, 8713
27. Garnier, J.; Kennedy, A. R.; Berlouis, L. E. A.; Turner, A. T.; Murphy, J. A. Beilstein J. Org. Chem. 2010, 6 73
28. Cahard, E.; Schoenebeck, F.; Garnier, J.; Cutulic, S. P. Y.; Zhou, S.; Murphy, J. A. Angew. Chem., Int. Ed. 2012, 51, 3673
29. Jolly, P. I.; Zhou, S.; Thomson, D. W.; Garnier, J.; Parkinson, J. A.; Tuttle, T.; Murphy, J. A. Chem. Sci. 2012, 3, 1675
30. Garnier, J.; Thomson, D. W.; Zhou, S.; Jolly, P. I.; Berlouis, L. E. A.; Murphy, J. A. Beilstein J. Org. Chem. 2012, 8, 994
31. Doni, E.; O'Sullivan, S.; Murphy, J. A. Angew. Chem., Int. Ed. 2013, 52, 2239
32. Tanko, J. M.; Li, X.; Chahma, M.; Jackson, W. F.; Spencer, J. N. J. Am. Chem. Soc. 2007, 129, 4181
33. Newcomb, M.; Toy, P. H. Acc. Chem. Res. 2000, 33, 449
34. Maslak, P.; Vallombroso, T. M.; Chapman, W. H., Jr.; Narvaez, J. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 73
35. Maslak, P.; Narvaez, J. N.; Vallombroso, T. M., Jr. J. Am. Chem. Soc. 1995, 117, 12373
36. Xu, Q.; Cheng, B.; Ye, X.; Zhai, H. Org. Lett. 2009, 11, 4136
37. For a discussion of π-stacking interactions, see: Hunter, C. A.; Sanders, J. M. K. J. Am. Chem. Soc. 1990, 112, 5525
38. Krollpfeiffer, F.; Rosenberg, A. Ber. Dtsch. Chem. Ges. 1936, 69, 465
39. Asensio, X.; Gonzalez-Lafont, A.; Marquet, J.; Lluch, J. M. J. Org. Chem. 2005, 70, 540
40. Fischer, H. Chem. Rev. 2001, 101, 3581
41. Studer, A. Chem. Soc. Rev. 2004, 33, 267
42. Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, 1133
43. Parr, R. G.; Yang, W. T. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
44. S. Grimme, S. J. Comput. Chem. 2006, 27, 1787
45. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
46. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639
47. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999
48. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
49. Kang, H.-Y.; Hong, W. S.; Cho, Y. S.; Koh, H. Y. Tetrahedron Lett. 1995, 36, 7661