Communications
d = 207.1, 173.2, 51.9, 42.5, 37.3, 27.9, 27.7, 15.79 ppm. The data was
Milstein, Angew. Chem. 2001, 113, 1153; Angew. Chem. Int. Ed.
2001, 40, 1119.
consistent to those reported in the literature.[7a]
[18]D. Milstein, Acc. Chem. Res. 1984, 17, 221.
[19]For an example of a spectroscopically characterized acyl–
hydrido species that undergoes intramolecular hydroacylation,
see: D. Milstein, J. Chem. Soc. Chem. Commun. 1982, 1357.
Received: August 2, 2006
Published online: October 17, 2006
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Keywords: C H activation · hemilabile ligands · homogeneous
catalysis · intermolecular hydroacylation · rhodium
.
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[1]For recent reviews on C H activation, see: a) V. Ritleng, C.
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1999, 111, 1808; Angew. Chem. Int. Ed. 1999, 38, 1698; d) Hand-
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book of C H Transformations: Applications in Organic Syn-
thesis (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005.
[2]K. Sakai, J. Ide, O. Oda, N. Nakamura, Tetrahedron Lett. 1972,
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[3]B. M. Trost, Acc. Chem. Res. 2002, 35, 695.
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Lett. 1991, 32, 3473; c) T. Sattelkau, P. Eilbracht, Tetrahedron
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Chem. Commun. 2005, 3307.
[5]For selected examples, see: a) Y. Sato, Y. Oonishi, M. Mori,
Angew. Chem. Int. Ed. 2002, 41, 1218; b) A. D. Aloise, M. E.
Layton, M. D. Shair, J. Am. Chem. Soc. 2000, 122, 12610;
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[6]For selected examples, see: a) T. B. Marder, D. C. Roe, D.
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[7]a) M. C. Willis, S. J. McNally, P. J. Beswick, Angew. Chem. Int.
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Woodward, G. S. Currie, Org. Lett. 2005, 7, 2249; c) M. C. Willis,
H. E. Randell-Sly, R. L. Woodward, S. J. McNally, G. S. Currie, J.
Org. Chem. 2006, 71, 5291.
[8]Although the dimer [{Rh(dppe)} 2](ClO4)2 (Ref. [4a]) can be
isolated, it is relatively air sensitive, and in our hands its use led
to variable results.
[9]M. C. Willis, S. Sapmaz, Chem. Commun. 2001, 2558.
[10]P. Braunstein, F. Naud, Angew. Chem. 2001, 113, 702; Angew.
Chem. Int. Ed. 2001, 40, 680.
[11]a) C. F. Lochow, R. G. Miller, J. Am. Chem. Soc. 1976, 98, 1281;
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[13]a) A. Macchioni, Chem. Rev. 2005, 105, 2039; b) E. Y. X. Chen,
T. J. Marks, Chem. Rev. 2000, 100, 1167.
[14]A catalyst generated from the direct combination of [{Rh-
(cod)Cl}2], dppe, and Ag(ClO4) was also active, although the
reaction required 4 h to reach completion.
[15]The product from entry 4 (Table 2) was obtained in 33% yield
with the original catalyst. See Ref. [7a].
[16]S.-M. Kuang, P. E. Fanwick, R. A. Walton, Inorg. Chem. 2002, 41,
405.
[17]a) J. W. Suggs, J. Am. Chem. Soc. 1978, 100, 640; b) C. Bianchini,
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ꢀ 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2006, 45, 7618 –7622