Organic Letters
Letter
Int. Ed. 2013, 52, 10573. (c) Liu, J.; Zheng, H.-X.; Yao, C.-Z.; Sun, B.-
F.; Kang, Y.-B. J. Am. Chem. Soc. 2016, 138, 3294−3297.
(4) Selected examples: (a) Oishi, T.; Yamaguchi, K.; Mizuno, N.
Angew. Chem., Int. Ed. 2009, 48, 6286. (b) Shimojo, H.; Moriyama, K.;
Togo, H. Synthesis 2013, 45, 2155. (c) Yin, W.; Wang, C.; Huang, Y.
Org. Lett. 2013, 15, 1850.
(5) Recent selected examples: (a) Ishihara, K.; Furuya, Y.;
Yamamoto, H. Angew. Chem., Int. Ed. 2002, 41, 2983. (b) Yamaguchi,
K.; Fujiwara, H.; Ogasawara, Y.; Kotani, M.; Mizuno, N. Angew. Chem.,
Int. Ed. 2007, 46, 3922. (c) Yu, L.; Li, H.; Zhang, X.; Ye, J.; Liu, J.; Xu,
Q.; Lautens, M. Org. Lett. 2014, 16, 1346.
(6) (a) Zhou, S.; Junge, K.; Addis, D.; Das, S.; Beller, M. Org. Lett.
2009, 11, 2461. (b) Sueoka, S.; Mitsudome, T.; Mizugaki, T.;
Jitsukawa, K.; Kaneda, K. Chem. Commun. 2009, 46, 8243.
(7) Hyodo, K.; Kitagawa, S.; Yamazaki, M.; Uchida, K. Chem. - Asian
J. 2016, 11, 1348.
(8) (a) Rokade, B. V.; Prabhu, K. R. J. Org. Chem. 2012, 77, 5364.
(b) Motiwala, H. F.; Yin, Q.; Aube,
(9) (a) Saednya, A. Synthesis 1982, 1982, 190. (b) Enthaler, S.;
́
J. Molecules 2016, 21, 45.
Weidauer, M.; Schroder, F. Tetrahedron Lett. 2012, 53, 882.
̈
(c) Zhuang, Y.-J.; Liu, J.; Kang, Y.-B. Tetrahedron Lett. 2016, 57, 5700.
(10) (a) Bellamy, F.; Martz, P.; Streith, J. Tetrahedron Lett. 1974, 15,
3189. (b) Miller, M. J.; Loudon, M. J. Org. Chem. 1975, 40, 126.
(c) Laulhe, S.; Gori, S.; Nantz, M. H. J. Org. Chem. 2012, 77, 9334.
(d) Quinn, D. J.; Haun, G. J.; Moura-Letts, G. Tetrahedron Lett. 2016,
57, 3844.
(11) (a) Lai, G.; Bhamare, N. K.; Anderson, W. K. Synlett 2001, 2,
230. (b) Erman, M. B.; Snow, J. W.; Williams, M. J. Tetrahedron Lett.
2000, 41, 6749. (c) Dornan, L. M.; Cao, Q.; Flanagan, J. C. A.;
Crawford, J. J.; Cook, M. J.; Muldoon, M. J. Chem. Commun. 2013, 49,
6030. For other example of nitrogen sources, see: (e) Kelly, C. B.;
Lambert, K. M.; Mercadante, M. A.; Ovian, J. M.; Bailey, W. F.;
Leadbeater, N. E. Angew. Chem., Int. Ed. 2015, 54, 4241.
(12) Yu et al. have achieved Brønsted acid catalyzed nitrile synthesis
for aliphatic aldehydes at ambient temperature; see: An, X. D.; Yu, S.
Org. Lett. 2015, 17, 5064.
(13) (a) Yamafuji, K. Nature 1953, 171, 745. (b) Yamafuji, K.;
Omura, H.; Yoshihara, F.; Yoshitake, M.; Oyama, N. Enzymol. 1958,
19, 180.
(14) Hyodo, K.; Togashi, K.; Oishi, N.; Hasegawa, G.; Uchida, K.
Green Chem. 2016, 18, 5788.
(15) MSH reagent (O-(mesitylsulfonyl)hydroxylamine): (a) Johnson,
C. R.; Kirchhoff, R. A.; Corkins, H. G. J. Org. Chem. 1974, 39, 2458.
(b) Grayson, E. J.; Bernardes, G. J. L.; Chalker, J. M.; Boutureira, O.;
Koeppe, J. R.; Davis, B. G. Angew. Chem., Int. Ed. 2011, 50, 4127.
HOSA (hydroxylamine O-sulfonic acid): (c) Brossi, A.; Minamikawa,
J. Org. Synth. 1978, 58, 32.
(16) O-(Diphenylphosphinyl)hydroxylamine (DPPH) and O-(2,4-
dinitrophenyl)hydroxylamine known as alternatives of MSH were used
instead of oxime 2c; however, nitrile 4a was not obtained at all, and
only corresponding oximes were observed.
(17) Selected examples: (a) Ramesh, C.; Banerjee, J.; Pal, R.; Das, B.
Adv. Synth. Catal. 2003, 345, 557. (b) Varghese, A.; Nizam, A.;
Kulkarni, R.; George, L. Eur. J. Chem. 2012, 3, 247.
(18) Wang, X.; Liu, R.; Jin, Y.; Liang, X. Chem. - Eur. J. 2008, 14,
2679.
(19) De Mico, A.; Margarita, R.; Parlanti, L.; Vescovi, A.; Piancatelli,
G. J. Org. Chem. 1997, 62, 6974.
(20) Chandrasekara Reddy, G.; Chandregowda, V.; Venkateswara
Rao, G. Heterocycles 2007, 71, 39.
(21) We also attempted to synthesize oxime 3ac; however, it
decomposed immediately.
(22) In the case using oxime 2c, nitrile 4a was smoothly formed
compared to using 2b, and the isotope effect was also shown, kH/kD =
D
Org. Lett. XXXX, XXX, XXX−XXX