Organic Letters
Letter
Soc. 2014, DOI: 10.1021/ja412578t. (e) Cabri, W.; Candiani, I.;
Colombo, M.; Franzoi, L.; Bedeschi, A. Tetrahedron Lett. 1995, 36,
REFERENCES
■
(1) (a) Ricci, A. Modern Amination Methods; Wiley: Weinheim, 2000.
(b) Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol.
Chem. 2006, 4, 2337. (c) Eller, K.; Henkes, E.; Rossbacher, R.; Hoke,
H. In Ullmann’s Encyclopedia of Industrial Chemistry; Wiley-VCH:
Weinheim, 2008; Vol. A2, p 2.
949. (f) A. Dahlen
7197. (g) Dahlen
, A.; Hilmersson, G. Chem.Eur. J. 2003, 9, 1123.
(14) (a) Szostak, M.; Spain, M.; Parmar, D.; Procter, D. J. Chem.
Commun. 2012, 48, 330. (b) Dahlen, A.; Hilmersson, G. Eur. J. Inorg.
́
, A.; Hilmersson, G. Tetrahedron Lett. 2002, 43,
́
̈
́
Chem. 2004, 3393. (c) Flowers, R. A., II Synlett 2008, 1427.
(15) (a) Parmar, D.; Price, K.; Spain, M.; Matsubara, H.; Bradley, P.
A.; Procter, D. J. J. Am. Chem. Soc. 2011, 133, 2418. (b) Parmar, D.;
Matsubara, H.; Price, K.; Spain, M.; Procter, D. J. J. Am. Chem. Soc.
2012, 134, 12751. (c) Sautier, B.; Lyons, S. E.; Webb, M. R.; Procter,
D. J. Org. Lett. 2012, 14, 146.
(2) (a) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I.,
Ed.; Pergamon Press: New York, 1991. (b) Hudlicky, M. Reductions in
Organic Chemistry; Ellis Horwood: Chichester, 1984. (c) Seyden-
Penne, J. Reductions by the Alumino- and Borohydrides in Organic
Synthesis; Wiley: New York, 1997. (d) Andersson, P. G.; Munslow, I. J.
Modern Reduction Methods; Wiley-VCH: Weinheim, 2008.
(3) Selected examples: (a) Haddenham, D.; Pasumansky, L.; DeSoto,
J.; Eagon, S.; Singaram, B. J. Org. Chem. 2009, 74, 1964. (b) Saavedra,
J. Z.; Resendez, A.; Rovira, A.; Eagon, S.; Haddenham, D.; Singaram,
B. J. Org. Chem. 2011, 77, 221. (c) Laval, S.; Dayoub, W.; Favre-
Reguillon, A.; Berthod, M.; Demonchaux, P.; Mignani, G.; Lemaire, M.
Tetrahedron Lett. 2009, 50, 7005. (d) Miao, X.; Bidange, J.; Dixneuf, P.
H.; Fischmeister, C.; Bruneau, C.; Dubois, J. L.; Couturier, J. L.
ChemCatChem 2012, 4, 1911. (e) Enthaler, S.; Addis, D.; Junge, K.;
Erre, G.; Beller, M. Chem.Eur. J. 2008, 14, 9491. (f) Werkmeister, S.;
Bornschein, C.; Junge, K.; Beller, M. Eur. J. Org. Chem. 2013, 3671.
(4) (a) Rappoport, Z. The Chemistry of the Cyano Group; Wiley
Interscience: New York, 1970. (b) Doumaux, A. R., Jr. J. Org. Chem.
1972, 37, 508.
(16) Szostak, M.; Spain, M.; Procter, D. J. J. Org. Chem. 2012, 77,
3049.
(17) Concellon
4493.
́
, J. M; Rodríguez-Solla, H. Chem.Eur. J. 2002, 8,
(5) (a) Rychnovsky, S. D.; Powers, J. P.; LePage, T. J. J. Am. Chem.
Soc. 1992, 114, 8375. (b) Marshall, J. A.; Bierenbaum, R. J. Org. Chem.
1977, 42, 3309. (c) Arapakos, P. G.; Scott, M. K.; Huber, F. E., Jr. J.
Am. Chem. Soc. 1969, 91, 2059.
(6) (a) Procter, D. J.; Flowers, R. A., II; Skrydstrup, T. Organic
Synthesis Using Samarium Diiodide: A Practical Guide; RSC Publishing:
Cambridge, 2009. (b) Kagan, H. B. Tetrahedron 2003, 59, 10351.
(c) Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104,
3371. (d) Nicolaou, K. C.; Ellery, S. P.; Chen, J. S. Angew. Chem., Int.
Ed. 2009, 48, 7140. (e) Szostak, M.; Procter, D. J. Angew. Chem., Int.
Ed. 2011, 50, 7737. (f) Szostak, M.; Spain, M.; Procter, D. J. Chem. Soc.
Rev. 2013, 42, 9155.
(7) Metal-mediated radical reactions: (a) Gansauer, A.; Bluhm, H.
̈
Chem. Rev. 2000, 100, 2771. (b) Szostak, M.; Procter, D. J. Angew.
Chem., Int. Ed. 2012, 51, 9238. (c) Streuff, J. Synthesis 2013, 45, 281.
(8) Hoz reported studies on the reduction of aromatic nitriles using
photostimulated Sm(II): (a) Rao, C. N.; Hoz, S. J. Org. Chem. 2012,
77, 4029. (b) Rao, C. N.; Hoz, S. J. Org. Chem. 2012, 77, 9199.
(9) Kamochi and Kudo described the reduction of aryl carboxylic
acid derivatives using SmI2; however, this process is low yielding and
limited in scope. (a) Kamochi, Y.; Kudo, T. Chem. Lett. 1993, 1495.
(b) Kamochi, Y.; Kudo, T. Bull. Chem. Soc. Jpn. 1992, 65, 3049.
(10) Reductive decyanation using SmI2 has been reported: Ricci, M.;
Blakskjaer, P.; Skrydstrup, T. J. Am. Chem. Soc. 2000, 122, 12413.
(11) Preparation of SmI2 in nitriles has been reported: Maisano, T.;
Tempest, K. E.; Sadasivam, D. V.; Flowers, R. A., II Org. Biomol. Chem.
2011, 9, 1714.
(12) For studies on SmI2−H2O, see: (a) Duffy, L. A.; Matsubara, H.;
Procter, D. J. J. Am. Chem. Soc. 2008, 130, 1136. (b) 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. (c) Guazzelli, G.;
De Grazia, S.; Collins, K. D.; Matsubara, H.; Spain, M.; Procter, D. J. J.
Am. Chem. Soc. 2009, 131, 7214. (d) Szostak, M.; Spain, M.; Procter,
D. J. Nat. Protoc. 2012, 7, 970. (e) Szostak, M.; Sautier, B.; Spain, M.;
Behlendorf, M.; Procter, D. J. Angew. Chem., Int. Ed. 2013, 52, 12559.
(f) Szostak, M.; Spain, M.; Procter, D. J. Angew. Chem., Int. Ed. 2013,
52, 7237. (g) Szostak, M.; Spain, M.; Choquette, K. A.; Flowers, R. A.,
II; Procter, D. J. J. Am. Chem. Soc. 2013, 135, 15702.
(13) For recent studies on SmI2−amine−H2O, see: (a) Szostak, M.;
Spain, M.; Procter, D. J. Chem. Commun. 2011, 47, 10254. (b) Szostak,
M.; Spain, M.; Procter, D. J. Org. Lett. 2012, 14, 840. (c) Szostak, M.;
Collins, K. D.; Fazakerley, N. J.; Spain, M.; Procter, D. J. Org. Biomol.
Chem. 2012, 10, 5820. For early studies with SmI2−NR3−H2O, see:
(d) Szostak, M.; Spain, M.; Eberhart, A. J.; Procter, D. J. J. Am. Chem.
1095
dx.doi.org/10.1021/ol403668e | Org. Lett. 2014, 16, 1092−1095