4144
L. Mantilli, C. Mazet / Tetrahedron Letters 50 (2009) 4141–4144
1991, 113, 958–967; (e) Tanaka, K.; Qiao, S.; Tobisu, M.; Lo, M. M.-C.; Fu, G. C. J.
Am. Chem. Soc. 2000, 122, 9870–9871; (f) Uma, R.; Davies, M. K.; Crévisy, C.;
Grée, R. Eur. J. Org. Chem. 2001, 3141–3146; (g) Martin-Matute, B.; Boga´r, K.;
Edin, M.; Kaynak, F. B.; Bäckvall, J. E. Chem. Eur. J. 2005, 11, 5832–5842; (h)
´
´
Cadierno, V.; Garcia-Garrido, S. E.; Gimeno, J.; Varela Alvarez, A.; Sordo, J. A. J.
Am. Chem. Soc. 2006, 128, 1360–1370; (i) Reetz, M. T.; Hougchao, G. Synlett
2006, 2127–2129.
2. For mechanistic studies, see: (a) Trost, B. M.; Kuliawec, R. J. J. Am. Chem. Soc.
1993, 115, 2027–2036; (b) McGrath, D. V.; Grubbs, R. H. Organometallics 1994,
13, 224–235; (c) Tanaka, K.; Fu, G. C. J. Org. Chem. 2001, 66, 8177–8186.
3. (a) Schrock, R. R.; Osborn, J. A. J. Am. Chem. Soc. 1976, 98, 2134–2143; (b) Chin,
C. S.; Shin, J. H.; Kim, C. J. Organomet. Chem. 1988, 356, 381–388; (c) Sun, Y.;
Landau, R. N.; Wang, J.; LeBlond, C.; Blackmond, D. G. J. Am. Chem. Soc. 1996,
118, 1348–1353.
4. Baudry, D.; Ephritikhine, M.; Felkin, H. Nouv. J. Chem. 1978, 2, 355–356.
5. Crabtree, R. H. Acc. Chem. Res. 1979, 12, 331–337.
6. Stork, G.; Kahne, D. J. Am. Chem. Soc. 1983, 105, 1072–1073.
7. Crabtree, R. H.; Davis, M. W. Organometallics 1983, 2, 681–682.
8. (a) Krel, M.; Lallemand, J.-Y.; Guillou, C. Synlett 2005, 2043–2046; (b) Kavanagh,
Y.; Chaney, C. M.; Muldoon, J.; Evans, P. J. Org. Chem. 2008, 73, 8601–8604; (c)
Fehr, C.; Farris, I. Angew. Chem. 2006, 118, 7058–7061; Angew. Chem. Int. Ed.
2006, 45, 6904–6907.
9. (a) Chin, C. S.; Park, J.; Kim, C.; Lee, S. Y.; Shin, J. H.; Kim, J. B. Catal. Lett. 1988, 1,
203–205; (b) Chin, C. S.; Lee, B. J. Chem. Soc., Dalton Trans. 1991, 1323–1327; (c)
Lu, X.; Lin, Y.; Ma, D. Pure Appl. Chem. 1988, 60, 1299–1306.
10. (a) Brookhart, M.; Grant, B.; Volpe, A. F. Organometallics 1992, 11, 3920–3922;
(b) Smidt, S. P.; Zimmermann, N.; Studer, M.; Pfaltz, A. Chem. Eur. J. 2004, 10,
4685–4693; (c) Vazquez-Serano, L. D.; Owens, B. T.; Buriak, J. M. Inorg. Chim.
Acta 2006, 359, 2786–2797; (d) Nama, D.; Butti, P.; Pregosin, P. S.
Organometallics 2007, 26, 4942–4954; (e) Wüstenberg, B.; Pfaltz, A. Adv.
Synth. Catal. 2008, 350, 174–178.
11. (a) Chodosh, D. F.; Crabtree, R. H.; Felkin, H.; Morris, G. E. J. Organomet. Chem.
1978, 161, C67–C70; (b) Wang, H.; Casalnuovo, A. L.; Johnson, B. J.; Mueting, A.;
Pignolet, L. H. Inorg. Chem. 1988, 27, 325–331; (c) Smidt, S. P.; Pfaltz, A.;
Martinez-Viviente, E.; Pregosin, P. S.; Albinati, A. Organometallics 2003, 22,
1000–1009; (d) Xu, Y.; Celik, M. A.; Thompson, A. L.; Cai, H.; Yurtsever, M.;
Odell, B.; Green, J. C.; Mingos, D. M. P.; Brown, J. M. Angew. Chem. 2009, 121,
590–593. Angew. Chem. Int. Ed. 2009, 48, 582–585.
12. See Supplementary data.
13. If the hydrogen atmosphere is maintained, the saturated alcohol is formed
preferentially. See Supplementary data.
14. For recent reviews: (a) Cui, X.; Burgess, K. Chem. Rev. 2005, 105, 3272–3296; (b)
Källström, K.; Munslow, I.; Andersson, P. G. Chem. Eur. J. 2006, 12, 3194–3200;
(c) Roseblade, S. J.; Pfaltz, A. Acc. Chem. Res. 2007, 40, 1402–1411.
15. Crabtree, R. H.; Demou, P. C.; Eden, D.; Mihelic, J.; Parnell, C. A.; Quirk, J. M.;
Morris, G. E. J. Am. Chem. Soc. 1982, 104, 6994–7001.
Figure 1. Labeling experiments using 1,1-dideuterated model substrate. The NMR
overlay shows the relative integration between C(3)H and C(2)H2 for all four
experiments.
Acknowledgments
This work was supported by the University of Geneva. We thank
D. Gérard and S. Torche for assistance in synthesis. Johnson-Matthey
is also thanked for generous loan of iridium precursors. Professor
E.-P. Kündig is warmly thanked for proofreading this Letter.
References and notes
1. For recent reviews, see: (a) Van der Drift, R. C.; Bouwman, E.; Drent, E. J.
Organomet. Chem. 2002, 650, 1–24; (b) Uma, R.; Crévisy, C.; Grée, R. Chem. Rev.
2003, 103, 27–52; (c) Cadierno, V.; Crochet, P.; Gimeno, J. Synlett 2008, 1105–
1124; For relevant examples, see: (d) Bergens, S.; Bosnich, B. J. Am. Chem. Soc.
16. For identification of iridium-dihydride intermediate A, see Supplementary
data.