Journal of the American Chemical Society
Page 4 of 5
mentals and Applications, 2nd ed.; John Wiley & Sons, Inc.: New York,
Int. Ed. 2012, 51, 5735. (c) Kuwano, S.; Harada, S.; Oriez, R.; Yamada,
1
2
3
4
5
6
7
8
NY, 2001. (g) Organic Electrochemistry, 4th ed., Lund, H.; Hammerich,
O.; Eds., M. Dekker, New York, NY, 2001. (h) Moeller, K. D. Tetrahe-
dron 2000, 56, 9527.
(2) Yoshida, J.-i.; Takada, K.; Ishichi, Y.; Isoe, S. J. Chem. Soc., Chem.
Commun. 1994, 2361.
K.-i. Chem. Commun. 2012, 48, 145. (d) De Sarkar, S.; Grimme, S.;
Studer, A. J. Am. Chem. Soc. 2010, 132, 1190. (e) Goswami, S.; Hazra,
A. Chem. Lett. 2009, 38, 484. (f) Yoshida, M.; Katagiri, Y.; Zhu, W.-B.;
Shishido, K. Org. Biomol. Chem. 2009, 7, 4062. (g) Wong, F. T.; Patra,
P. K.; Seayad, J.; Zhang, Y.; Ying, J. Y. Org. Lett. 2008, 10, 2333. (h)
Maki, B. E.; Scheidt, K. A. Org. Lett. 2008, 10, 4331. (i) Noonan, C.;
Baragwanath, L.; Connon, S. J. Tetrahedron Lett. 2008, 49, 4003. (j)
Guin, J.; De Sarkar, S.; Grimme, S.; Studer, A. Angew. Chem. Int. Ed.
2008, 47, 8727. (k) Liu, Y.-K.; Li, R.; Yue, L.; Li, B.-J.; Chen, Y.-C.;
Wu, Y.; Ding, L.-S. Org. Lett. 2006, 8, 1521. (l) Miyashita, A.; Suzuki,
Y.; Nagasaki, I.; Ishiguro, C.; Iwamoto, K.-i.; Higashino, T. Chem.
Pharm. Bull. 1997, 45, 1254.
(3)
For electrochemical oxidation of aldehydes to esters in the
presence of cyanide anion, see: Chiba, T.; Okimoto, M.; Nagai, H.;
Takata, Y. Bull. Chem. Soc. Jpn. 1982, 55, 335.
(4)
(a) Ho, X.-H.; Mho, S.-i.; Kang, H.; Jang, H.-Y. Eur. J. Org.
9
Chem. 2010, 4436. (b) Bui, N.-N.; Ho, X.-H.; Mho, S.-i.; Jang, H.-Y. Eur.
J. Org. Chem. 2009, 5309.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(5)
(a) Xu, H.-C.; Moeller, K. D. J. Am. Chem. Soc. 2008, 130,
13542. (b) Tang, F.; Moeller, K. D. J. Am. Chem. Soc. 2007, 129, 12414.
(c) Miura, T.; Kim, S.; Kitano, Y.; Tada, M.; Chiba, K. Angew. Chem.
Int. Ed. 2006, 45, 1461. (d) Liu, B.; Duan, S.; Sutterer, A. C.; Moeller,
K. D. J. Am. Chem. Soc. 2002, 124, 10101. (e) Duan, S.; Moeller, K. D.
Org. Lett. 2001, 3, 2685.
(13)
For examples and mechanistic investigation of NHC-
catalyzed aerobic oxidation of aldehydes, see: Chiang, P.-C.; Bode, J.
W. Org. Lett. 2011, 13, 2422.
(14)
For a recent review, see: Vora, H. U.; Wheeler, P.; Rovis, T.
Adv. Synth. Catal. 2012, 354, 1617. For excellent recent examples, see:
(a) Zhang, B.; Feng, P.; Cui, Y.; Jiao, N. Chem. Commun. 2012, in press
(DOI: 10.1039/c2cc32862c). (b) Feroci, M.; Chiarotto, I.; Orsini, M.;
Pelagalli, R.; Inesi, A. Chem. Commun. 2012, 48, 5361. (c) Zhao, Y.-M.;
Tam, Y.; Wang, Y.-J.; Li, Z.; Sun, J. Org. Lett. 2012, 14, 1398. (d) Sohn,
S. S.; Bode, J. W. Angew. Chem. Int. Ed. 2006, 45, 6021. (e) Chan, A.;
Scheidt, K. A. Org. Lett. 2005, 7, 905. (f) Reynolds, N.; Alaniz, J.; Rovis,
T. J. Am. Chem. Soc. 2004, 126, 9518. (g) Sohn, S. S.; Rosen, E. L.;
Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370. (h) Chow, K. Y.-K.;
Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126.
(15)
2010, 51, 1786.
(16)
(17)
1958, 80, 4300.
(6)
(7)
Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
For electrochemical oxidation of aldehydes to esters via
hemiacetal intermediates using halide mediators, see: (a) Shono, T.;
Matsumura, Y.; Hayashi, J.; Inoue, K.; Iwasaki, F.; Itoh, T. J. Org. Chem.
1985, 50, 4967. (b) Okimoto, M.; Chiba, T. J. Org. Chem. 1988, 53,
218.
(8)
For an example of organocatalyzed reductive coupling of
carboxylates, see: Costero, A. M.; Rodríguez-Muñiz, G. M.; Gaviña, P.;
Gil, S.; Domenech, A. Tetrahedron Lett. 2007, 48, 6992.
(9)
(a) DiRocco, D. A.; Oberg, K. M.; Rovis, T. J. Am. Chem Soc.
Shimakawa, Y.; Morikawa, T.; Sakaguchi, S. Tetrahedron Lett.
2012, 134, 6143. (b) Nakanishi, I.; Itoh, S.; Fukuzumi, S. Chem. Eur. J.
1999, 5, 2810. (c) Barletta, G.; Chung, A. C.; Rios, C. B.; Jordan, F.;
Schlegel, J. M. J. Am. Chem. Soc. 1990, 112, 8144.
Vaska, L.; DiLuzio, J. W. J. Am. Chem. Soc. 1969, 84, 679.
Yang, J. Y.; McEwen, W. E.; Kleinberg, J. J. Am. Chem. Soc.
(10)
(a) Tam-Chang, S.-W.; Jimenez, L.; Diederich, F. Helv. Chim.
Acta 1993, 76, 2616. (b) Tam, S.-W.; Jimenez, L.; Diederich, F. J. Am.
Chem. Soc. 1992, 114, 1503.
(18)
(a) Chiang, P.-C.; Bode, J. W. in N-Heterocyclic Carbenes: From
Laboratory Curiosities to Efficient Synthetic Tools; Díez-Gonzáles, S.; Ed.;
RSC Catalysis Series No. 6; Royal Society of Chemistry: Cambridge,
2010; pp 399-435. (b) Moore, J. L.; Rovis, T. Top. Curr. Chem. 2009,
291, 77. (c) Enders, D.; Niemeier, O., Henseler, A. Chem. Rev. 2007,
107, 5606.
(11)
For additional information on electrochemical mediators,
see: (a) ref 1g, chapters 1 and 29. (b) Ogibin, Y. N.; Elinson, M. N.;
Nikishin, G. I. Russ. Chem. Rev. 2009, 78, 89. (c) Wu, X.; Davis, A. P.;
Lambert, P. C.; Steffen, L. K.; Toy, O.; Fry, A. J. Tetrahedron 2009, 65,
2408. (d) Steckhan, E. Top. Curr. Chem. 1987, 142, 1. (e) Steckhan, E.
Angew. Chem. Int. Ed. Engl. 1986, 25, 683.
(19)
37, 8317.
Frey, D. A.; Wu, N.; Moeller, K. D. Tetrahedron Lett. 1996,
(12)
(a) Biswas, A.; De Sarkar, S.; Tebben, L.; Studer, A. Chem.
Commun. 2012, 48, 5190. (b) Lee, K.; Kim, H.; Hong, J. Angew. Chem.
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