Tom S. Carter et al.
COMMUNICATIONS
Oldenburg, L. Que Jr, Angew. Chem. 2008, 120, 1913;
Angew. Chem. Int. Ed. 2008, 47, 1887; e) O. Bistri, A.
Correa, C. Bolm, Angew. Chem. 2008, 120, 596; Angew.
Chem. Int. Ed. 2008, 47, 586; f) J. Bonnamour, C.
Bolm, Org. Lett. 2008, 10, 2665; g) A. Correa, M.
Carril, C. Bolm, Angew. Chem. 2008, 120, 2922; Angew.
Chem. Int. Ed. 2008, 47, 2880; h) M. Carril, A. Correa,
C. Bolm, Angew. Chem. 2008, 120, 4940; Angew. Chem.
Int. Ed. 2008, 47, 4862.
kovsky, P. J. Chirik, Inorg. Chem. 2006, 45, 7252;
d) S. C. Bart, K. Chlopek, E. Bill, M. W. Bouwkamp, E.
Lobkovsky, F. Neese, K. Wieghardt, P. J. Chirik, J. Am.
Chem. Soc. 2006, 128, 13901; e) R. J. Trovitch, E. Lob-
kovsky, E. Bill, P. J. Chirik, Organometallics 2008, 27,
1470. f) Following the submission of this communica-
tion Chirik and co-workers reported the Fe(0)-cata-
lysed reduction of 3 trisubstituted alkenes, see: R. P.
Yu, J. M. Darmon, J. M. Hoyt, G. W. Margulieux, Z. R.
Turner, P. J. Chirik, ACS Catalysis 2012, 2, 1760..
[10] a) C. Rangheard, C. de J. Fernꢆndez, P.-H. Phua, J.
Hoorn, L. Lefort, J. G. de Vries, Dalton Trans. 2010, 39,
8464; b) P.-H. Phua, L. LeFort, J. A. F. Boogers, M.
Tristany, J. G. de Vries, Chem. Commun. 2009, 3747.
[11] a) M. Takeuchi, K. Kano, Organometallics 1993, 12,
2059; b) S. Sakaki, T. Kojima, T. Arai, J. Chem. Soc.
Dalton Trans. 1994, 7.
[6] a) S. C. Bart, E. Lobkovsky, P. J. Chirik, J. Am. Chem.
Soc. 2004, 126, 13794; b) A. M. Archer, M. W. Bouw-
kamp, M.-P. Cartez, E. Lobkovshy, P. J. Chirik, Organo-
metallics 2006, 25, 4269.
[7] For reviews see: a) K. Junge, K. Schrçder, M. Beller,
Chem. Commun. 2011, 47, 4849; b) P. J. Chirik, in: Cat-
alysis without Precious Metals, (Ed.: R. M. Bullock),
Wiley-VCH, Weinheim, 2010, pp 83–110; c) S. Chakra-
borty, H. Guan Dalton Trans. 2010, 39, 7427; d) C.
Wang, X. F. Wu, J. L. Xiao, Chem. Asian J. 2008, 3,
1750. For selected recent examples, see: e) R. Langer,
G. Leitus, Y. Ben-David, D. Milstein, Angew. Chem.
2011, 123, 2168; Angew. Chem. Int. Ed. 2011, 50, 2120;
f) P. O. Lagaditis, A. J. Lough, R. H. Morris, J. Am.
Chem. Soc. 2011, 133, 9662; g) P. O. Lagaditis, A. J.
Lough, R. H. Morris, Inorg. Chem. 2010, 49, 10057;
h) A. A. Mikhailine, R. H. Morris, Inorg. Chem. 2010,
49, 11039; i) R. H. Morris, Chem. Soc. Rev. 2009, 38,
2282; j) S. Enthaler, K. Junge, M. Beller, Angew. Chem.
2008, 120, 3363; Angew. Chem. Int. Ed. 2008, 47, 3317;
k) C. P. Casey, H. Guan, J. Am. Chem. Soc. 2007, 129,
5816.
[12] S. Sakaki, T. Sagara, T. Arai, T. Kojima, T. Ogata, K.
Ohkubo, J. Mol. Catal. 1992, 75, 33.
[13] a) E. C. Ashby, J. J. Lin, Tetrahedron Lett. 1977, 18,
4481; b) E. C. Ashby, J. J. Lin, J. Org. Chem. 1978, 43,
2567.
[14] E. K. Leggans, T. J. Barker, K. K. Duncan, D. L. Boger,
Org. Lett. 2012, 14, 1428.
[15] B. A. F. Le Bailly, M. D. Greenhalgh, S. P. Thomas,
Chem. Commun. 2012, 48, 1580.
[16] G. N. Glavee, K. J. Klabunde, C. M. Sorensen, G. C.
Hadjipanayis, Inorg. Chem. 1995, 34, 28.
[17] See the Supporting Information for details.
[18] a) W. M. Czaplik, S. Grupe, M. Mayer, A. Jacobi von
Wangelin, Chem. Commun. 2010, 46, 6350; b) A. Fꢄrst-
ner, R. Martin, H. Krause, G. Seidel, R. Goddard,
C. W. Lehmann, J. Am. Chem. Soc. 2008, 130, 8773;
c) B. Bogdanovic, M. Schwickardi, Angew. Chem. 2000,
112, 4788; Angew. Chem. Int. Ed. 2000, 39, 4610.
[19] D. Zhang, J. M. Ready, J. Am. Chem. Soc. 2006, 128,
15050.
[8] a) E. N. Frenkel, E. A. Emken, H. M. Peters, V. L. Da-
vidson, R. O. Butterfield, J. Org. Chem. 1964, 29, 3292;
b) M. A. Schroeder, M. S. Wrighton, J. Organomet.
Chem. 1977, 128, 345; c) M. Cais, N. J. Maoz, J. Chem.
Soc. A 1971, 11, 1811; d) E. J. Daida, J. C. Peters, Inorg.
Chem. 2004, 43, 7474.
[9] a) A. M. Tondreau, E. Lobkovsky, P. J. Chirik, Org.
Lett. 2008, 10, 2789; b) A. M. Tondreau, J. M. Darmon,
B. M. Wile, S. K. Floyd, E. Lobkovsky, P. J. Chirik, Or-
ganometallics 2009, 28, 3928; c) R. J. Trovitch, E. Lob-
[20] a) C. Bianchini, A. Meli, M. Perzuzzini, F. Vizza, F. Za-
nobini, P. Frediani, Organometallics 1989, 8, 2080; b) S.
Enthaler, M. Haberberger, E. Irran, Chem. Asian J.
2011, 6, 1613.
884
ꢂ 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2013, 355, 880 – 884