656
J. Burnley et al.
LETTER
(15) Benati, L.; Bencivenni, G.; Leardini, R.; Minozzi, M.;
Nanni, D.; Scialpi, R.; Spagnolo, P.; Zanardi, G. J. Org.
Chem. 2006, 71, 5822.
(16) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635.
(17) (a) Guthrie, R. D.; Nutter, D. L. Bull. Soc. Chim. Belg. 1982,
91, 455. (b) Guthrie, R. D.; Nutter, D. L. J. Am. Chem. Soc.
1982, 104, 7478.
(18) Guthrie, R. D. J. Org. Chem. 1975, 40, 402.
(19) Russel, G. A.; Janzen, E. G.; Strom, E. T. J. Am. Chem. Soc.
1964, 86, 1807.
(20) Inoue, H.; Higashiura, K. J. Chem. Soc., Chem. Commun.
1980, 549.
(6) (a) Kolb, H. C.; Sharpless, K. B. Drug Discov. Today 2003,
8, 1128. (b) Moorhouse, A. D.; Spiteri, C.; Sharma, P.; Zloh,
M.; Moses, J. E. Chem. Commum. 2011, 47, 230.
(c) Moorhouse, A. D.; Santos, A. M.; Gunaratnam, M.;
Moore, M.; Neidle, S.; Moses, J. E. J. Am. Chem. Soc. 2006,
128, 15972.
(7) For some selected publications regarding the radical
chemistry of azides, see: (a) Benati, L.; Montevecchi, P. C.
J. Org. Chem. 1981, 46, 4570. (b) Kim, S.; Joe, G. H.; Do, J.
Y. J. Am. Chem. Soc. 1994, 116, 5521. (c) Montevecchi, P.
C.; Navacchia, M. L.; Spagnolo, P. Eur. J. Org. Chem. 1998,
1219. (d) Benati, L.; Leardini, R.; Minozzi, M.; Nanni, D.;
Spagnolo, P.; Strazzi, S.; Zanardi, G. Org. Lett. 2002, 4,
3079. (e) Renaud, P.; Olliver, C. J. Am. Chem. Soc. 2001,
123, 4717. (f) Renaud, P.; Olliver, C.; Panchaud, P. Angew.
Chem. Int. Ed. 2002, 41, 3460.
(8) (a) Barral, K.; Moorhouse, A. D.; Moses, J. E. Org. Lett.
2007, 9, 1809. (b) Moorhouse, A. D.; Moses, J. E. Synlett
2008, 2089. (c) Zhang, F.; Moses, J. E. Org. Lett. 2009, 11,
1587. (d) Sharma, P.; Moorhouse, A. D.; Moses, J. E. Synlett
2011, 2384.
(9) Warrier, M.; Lo, M. K. F.; Monbouquette, H.; Garcia-
Garibay, M. A. Photochem. Photobiol. Sci. 2004, 3, 859.
(10) Herbranson, D. E.; Hawley, M. D. J. Org. Chem. 1990, 55,
4297.
(21) No reduction product was observed when the reaction
mixture was heated at 50 °C.
(22) (a) Khramov, D. M.; Bielawski, C. W. Chem. Commum.
2005, 4958. (b) Khramov, D. M.; Bielawski, C. W. J. Org.
Chem. 2007, 9407. (c) Coady, D. J.; Khramov, D. M.;
Norris, B. C.; Tennyson, A. G.; Bielawski, C. W. Angew.
Chem. Int. Ed. 2009, 48, 5187.
(23) (a) Canal, J. P.; Ramnial, T.; Dickie, D. A.; Clyburne, J. A.
C. Chem. Commun. 2006, 1809. (b) Hahn, F. E. Angew.
Chem. Int. Ed. 2006, 45, 1348. (c) Crabtree, R. H. J.
Organomet. Chem. 2005, 690, 5451. (d) Herrmann, W. A.;
Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
(e) Arduengo, A. J. III. Acc. Chem. Res. 1999, 32, 913.
(f) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G.
Chem. Rev. 2000, 100, 39.
(11) Gartiser, T.; Selve, C.; Delpuech, J.-J. Tetrahedron Lett.
1983, 24, 1609.
(12) Boyer, J. H. J. Am. Chem. Soc. 1951, 71, 5865.
(13) Rolla, F. J. Org. Chem. 1982, 47, 4327.
(24) Chen, Y.; Kamlet, A. S.; Steinman, J. B.; Liu, D. R. Nat.
Chem. 2011, 3, 146.
(14) (a) Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 2796.
(b) Benati, L.; Bencivenni, G.; Leardini, R.; Minozzi, M.;
Nanni, D.; Scialpi, R.; Spagnolo, P.; Zanardi, G. J. Org.
Chem. 2005, 70, 3046.
(25) Maejima, T.; Shimoda, Y.; Nozaki, K.; Mori, S.; Sawama,
Y.; Monguchi, Y.; Sajiki, H. Tetrahedron 2012, 68, 1712.
Synlett 2013, 24, 652–656
© Georg Thieme Verlag Stuttgart · New York