Proton-Coupled Electron Transfer in the Reduction of Arenes by SmI2-Water Complexes

Journal of the American Chemical Society

Volumn 137, Issue 35, 2015, Pages 11526-11531

  Chciuk, Tesia V ^a   Flowers, Robert A ^a  

^a LEHIGH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; BOND STRENGTH (CHEMICAL); ELECTRON TRANSITIONS; REDUCTION;

BOND DISSOCIATION ENERGIES; BOUND WATERS; ELECTRON TRANSFER; PRESENCE OF WATER; PROTON COUPLED ELECTRON TRANSFERS; REDUCING SYSTEMS; THERMOCHEMICAL DATA; WATER COMPLEXES;

SAMARIUM COMPOUNDS;

ANTHRACENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; PROTON; WATER;

ARTICLE; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); DISSOCIATION; ELECTRON TRANSPORT; HYDROGEN BOND; HYDROPHILICITY; PROTON TRANSPORT; REDUCTION;

EID: 84941213911     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b07518     Document Type: Article

References (83)

1. Szostak, M.; Spain, M.; Parmar, D.; Procter, D. J. Chem. Commun. 2012, 48, 330-346 10.1039/C1CC14252F
2. Flowers, R. A., II Synlett 2008, 2008, 1427-1439 10.1055/s-2008-1078414
3. Dahlen, A.; Hilmersson, G. Eur. J. Inorg. Chem. 2004, 2004, 3393-3403 10.1002/ejic.200400442
4. Choquette, K. A.; Flowers, R. A. Sm and Yb Reagents. In Comprehensive Organic Synthesis, 2nd ed.; Molander, G. A.; Knochel, P., Eds.; Elsevier: Oxford, 2014; Vol. 1, pp 279-343.
5. Szostak, M.; Fazakerley, N. J.; Parmar, D.; Procter, D. J. Chem. Rev. 2014, 114, 5959-6039 10.1021/cr400685r
6. Szostak, M.; Spain, M.; Procter, D. J. Chem. Soc. Rev. 2013, 42, 9155-9183 10.1039/c3cs60223k
7. Procter, D. J.; Flowers, R. A., II; Skrydstrup, T. Organic Synthesis using Samarium Diiodide: A Practical Guide; RSC Publishing: Cambridge, 2010.
8. Nicolaou, K. C.; Ellery, S. P.; Chen, J. S. Angew. Chem., Int. Ed. 2009, 48, 7140-7165 10.1002/anie.200902151
9. Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104, 3371-3404 10.1021/cr030017a
10. Kagan, H. B. Tetrahedron 2003, 59, 10351-10372 10.1016/j.tet.2003.09.101
11. Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727-2884 10.1039/a908189e
12. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338 10.1021/cr950019y
13. Molander, G. A. Chem. Rev. 1992, 92, 29-68 10.1021/cr00009a002
14. Hoz, S.; Yacovan, A.; Bilkis, I. J. Am. Chem. Soc. 1996, 118, 261-262 10.1021/ja950937d
15. Chopade, P. R.; Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2004, 126, 44-45 10.1021/ja038363x
16. Sautier, B.; Procter, D. J. Chimia 2012, 66, 399-403 10.2533/chimia.2012.399
17. Hasegawa, E.; Curran, D. P. J. Org. Chem. 1993, 58, 5008-5010 10.1021/jo00070a046
18. Tarnopolsky, A.; Hoz, S. J. Am. Chem. Soc. 2007, 129, 3402-3407 10.1021/ja0686662
19. Tarnopolsky, A.; Hoz, S. Org. Biomol. Chem. 2007, 5, 3801-3804 10.1039/b713014g
20. Amiel-Levy, M.; Hoz, S. J. Am. Chem. Soc. 2009, 131, 8280-8284 10.1021/ja9013997
21. Prasad, E.; Flowers, R. A., II J. Am. Chem. Soc. 2005, 127, 18093-18099 10.1021/ja056352t
22. Kamochi, Y.; Kudo, T. Chem. Lett. 1991, 893-896 10.1246/cl.1991.893
23. Kamochi, Y.; Kudo, T. Bull. Chem. Soc. Jpn. 1992, 65, 3049-3054 10.1246/bcsj.65.3049
24. Kamochi, Y.; Kudo, T. Chem. Lett. 1993, 1495-1498 10.1246/cl.1993.1495
25. Duffy, L. A.; Matsubara, H.; Procter, D. J. J. Am. Chem. Soc. 2008, 130, 1136-1137 10.1021/ja078137d
26. Guazzelli, G.; De Grazia, S.; Collins, K. D.; Matsubara, H.; Spain, M.; Procter, D. J. J. Am. Chem. Soc. 2009, 131, 7214-7215 10.1021/ja901715d
27. Parmar, D.; Duffy, L. A.; Sadasivam, D. V.; Matsubara, H.; Bradley, P. A.; Flowers, R. A., II; Procter, D. J. J. Am. Chem. Soc. 2009, 131, 15467-15473 10.1021/ja906396u
28. Szostak, M.; Spain, M.; Procter, D. J. Chem. Commun. 2011, 47, 10254-10256 10.1039/c1cc14014k
29. Szostak, M.; Spain, M.; Procter, D. J. Org. Lett. 2012, 14, 840-843 10.1021/ol203361k
30. Szostak, M.; Collins, K. D.; Fazakerley, N. J.; Spain, M.; Procter, D. J. Org. Biomol. Chem. 2012, 10, 5820-5824 10.1039/c2ob00017b
31. Szostak, M.; Sautier, B.; Spain, M.; Behlendorf, M.; Procter, D. J. Angew. Chem., Int. Ed. 2013, 52, 12559-12563 10.1002/anie.201306484
32. Szostak, M.; Spain, M.; Choquette, K. A.; Flowers, R. A., II; Procter, D. J. J. Am. Chem. Soc. 2013, 135, 15702-15705 10.1021/ja4078864
33. Szostak, M.; Spain, M.; Eberhart, A. J.; Procter, D. J. J. Am. Chem. Soc. 2014, 136, 2268-2271 10.1021/ja412578t
34. Szostak, M.; Spain, M.; Procter, D. J. J. Am. Chem. Soc. 2014, 136, 8459-8466 10.1021/ja503494b
35. Szostak, M.; Spain, M.; Eberhart, A. J.; Procter, D. J. J. Org. Chem. 2014, 79, 11988-12003 10.1021/jo5018525
36. Just-Baringo, X.; Procter, D. J. Acc. Chem. Res. 2015, 48, 1263-1275 10.1021/acs.accounts.5b00083
37. Enemaerke, R. J.; Daasbjerg, K.; Skrydstrup, T. Chem. Commun. 1999, 343-344 10.1039/a809277j
38. Miller, R. S.; Sealy, J. M.; Fuchs, J. R.; Shabangi, M.; Flowers, R. A., II J. Am. Chem. Soc. 2000, 122, 7718-7722 10.1021/ja001260j
39. Andrieux, C. P.; Gallardo, I.; Saveant, J.-M. J. Am. Chem. Soc. 1989, 111, 1620-1626 10.1021/ja00187a014
40. Saveant, J.-M. J. Am. Chem. Soc. 1992, 114, 10595-10602 10.1021/ja00052a065
41. Prasad, E.; Flowers, R. A., II J. Am. Chem. Soc. 2002, 124, 6895-6899 10.1021/ja026074n
42. Szostak, M.; Spain, M.; Procter, D. J. J. Org. Chem. 2014, 79, 2522-2537 10.1021/jo4028243
43. Vanýsek, P. CRC Handbook of Chemistry and Physics, 85th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 2004-2005; pp 1264-1266.
44. Isse, A. A.; Lin, C. Y.; Coote, M. L.; Gennaro, A. J. Phys. Chem. B 2011, 115, 678-684 10.1021/jp109613t
45. Shabangi, M.; Sealy, J. M.; Fuchs, J. R.; Flowers, R. A., II Tetrahedron Lett. 1998, 39, 4429-4432 10.1016/S0040-4039(98)00839-9
46. Teprovich, J. A., Jr.; Balili, M. N.; Pintauer, T.; Flowers, R. A., II Angew. Chem., Int. Ed. 2007, 46, 8160-8163 10.1002/anie.200702571
47. Sadasivam, D. V.; Teprovich, J. A., Jr.; Procter, D. J.; Flowers, R. A., II Org. Lett. 2010, 12, 4140-4143 10.1021/ol101722c
48. Neverov, A. A.; Gibson, G.; Brown, R. S. Inorg. Chem. 2003, 42, 228-234 10.1021/ic0203769
49. Bank, S.; Bockrath, B. J. Am. Chem. Soc. 1972, 94, 6076-6083 10.1021/ja00772a023
50. Minnich, E. R.; Long, L. D.; Ceraso, J. M.; Dye, J. L. J. Am. Chem. Soc. 1973, 95, 1061-1070 10.1021/ja00785a012
51. Papadakis, N.; Dye, J. L. J. Phys. Chem. 1978, 82, 1111-1114 10.1021/j100499a004
52. Nielsen, M. F.; Ingold, K. U. J. Am. Chem. Soc. 2006, 128, 1172-1182 10.1021/ja0548081
53. Plata, R. E.; Singleton, D. A. J. Am. Chem. Soc. 2015, 137, 3811-3826 10.1021/ja5111392
54. Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363-390 10.1146/annurev.physchem.55.091602.094446
55. Roth, J. P.; Mayer, J. M. Inorg. Chem. 1999, 38, 2760-2761 10.1021/ic990251c
56. Manner, V. W.; Mayer, J. M. J. Am. Chem. Soc. 2009, 131, 9874-9875 10.1021/ja902942g
57. Fang, H.; Ling, Z.; Lang, K.; Brothers, P. J.; Bruin, B.; Fu, X. Chem. Sci. 2014, 5, 916-921 10.1039/C3SC52326H
58. Wu, A.; Mayer, J. M. J. Am. Chem. Soc. 2008, 130, 14745 10.1021/ja805067h
59. Wu, A.; Masland, J.; Swartz, R. D.; Kaminsky, W.; Mayer, J. M. Inorg. Chem. 2007, 46, 11190-11201 10.1021/ic7015726
60. Milsmann, C.; Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2014, 136, 12099-12107 10.1021/ja5062196
61. Estes, D. P.; Grills, D. C.; Norton, J. R. J. Am. Chem. Soc. 2014, 136, 17362-17365 10.1021/ja508200g
62. Ruscic, B.; Wagner, A. F.; Harding, L. B.; Asher, R. L.; Feller, D.; Dixon, D. a.; Peterson, K. a.; Song, Y.; Qian, X.; Ng, C. Y.; Liu, J.; Chen, W.; Schwenke, D. W. J. Phys. Chem. A 2002, 106, 2727-2747 10.1021/jp013909s
63. Stein, S. E.; Brown, R. L. J. Am. Chem. Soc. 1991, 113, 787-793 10.1021/ja00003a009
64. Spiegel, D. A.; Wiberg, K. B.; Schacherer, L. N.; Medeiros, M. R.; Wood, J. L. J. Am. Chem. Soc. 2005, 127, 12513-12515 10.1021/ja052185l
65. Pozzi, D.; Scanlan, E. M.; Renaud, P. J. Am. Chem. Soc. 2005, 127, 14204-14205 10.1021/ja055691j
66. Jonas, R. T.; Stack, T. D. P. J. Am. Chem. Soc. 1997, 119, 8566-8567 10.1021/ja971503g
67. Cuerva, J. M.; Campana, A. G.; Justicia, J.; Rosales, A.; Oller-Lopez, J. L.; Robles, R.; Cardenas, D. J.; Bunuel, E.; Oltra, J. E. Angew. Chem., Int. Ed. 2006, 45, 5522-5526 10.1002/anie.200600831
68. Paradas, M.; Campaña, A. G.; Jiménez, T.; Robles, R.; Oltra, J. E.; Buñuel, E.; Justicia, J.; Cárdenas, D. J.; Cuerva, J. M. J. Am. Chem. Soc. 2010, 132, 12748-12756 10.1021/ja105670h
69. Tarantino, K. T.; Miller, D. C.; Callon, T. A.; Knowles, R. R. J. Am. Chem. Soc. 2015, 137, 6440-6443 10.1021/jacs.5b03428
70. Melander, L.; Saunders, W. J., Jr. Reaction Rates of Isotopic Molecules; John Wiley & Sons: New York, 1980.
71. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006.
72. Edwards, S. J.; Soudackov, A. V.; Hammes-Schiffer, S. J. Phys. Chem. A 2009, 113, 2117-2126 10.1021/jp809122y
73. Hammes-Schiffer, S. J. Am. Chem. Soc. 2015, 137, 8860-8871 10.1021/jacs.5b04087
74. Warren, J. J.; Menzeleev, A. R.; Kretchmer, J. S.; Miller, T. F., III; Gray, H. B.; Mayer, J. M. J. Phys. Chem. Lett. 2013, 4, 519-523 10.1021/jz400029w
75. Megiatto, J. D., Jr.; Méndez-Hernández, D. D.; Tejeda-Ferrari, M. E.; Teillout, A.-L.; Llansola-Portolés, M. J.; Kodis, G.; Poluektov, O. G.; Rajh, T.; Mujica, V.; Groy, T. L.; Gust, D.; Moore, T. A.; Moore, A. L. Nat. Chem. 2014, 6, 423-428 10.1038/nchem.1862
76. Warren, J. J.; Mayer, J. M. J. Am. Chem. Soc. 2011, 133, 8544-8551 10.1021/ja201663p
77. Schrauben, J. N.; Cattaneo, M.; Day, T. C.; Tenderholt, A. L.; Mayer, J. M. J. Am. Chem. Soc. 2012, 134, 16635-16645 10.1021/ja305668h
78. Tarantino, K. T.; Liu, P.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 10022-10025 10.1021/ja404342j
79. Robinson, J. R.; Gordon, Z.; Booth, C. H.; Carroll, P. J.; Walsh, P. J.; Schelter, E. J. J. Am. Chem. Soc. 2013, 135, 19016-19024 10.1021/ja410688w
80. Chciuk, T. V.; Hilmersson, G.; Flowers, R. A., II J. Org. Chem. 2014, 79, 9441-9443 10.1021/jo501819z
81. Chopade, P.; Davis, T. A.; Prasad, E.; Flowers, R. A., II Org. Lett. 2004, 6, 2685-2688 10.1021/ol049129u
82. Evans, W. J.; Gonzales, S. L.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2600-2608 10.1021/ja00085a046
83. Fedushkin, I. L.; Bochkarev, M. N.; Dechert, S.; Schumann, H. Chem.-Eur. J. 2001, 7, 3558-3563 10.1002/1521-3765(20010817)7:16<3558::AID-CHEM3558>3.0.CO;2-H