COMMUNICATIONS
Rhodium(I)-Catalyzed Intermolecular Hydroacylation of a-Keto Amides
[4] S. P. Curran, S. J. Connon, Org. Lett. 2012, 14, 1074–
1077.
[5] For a recent review, see: K. Riener, M. P. Hçgerl, P.
Brayshaw, A. S. Weller, M. C. Willis, Chem. Eur. J.
2008, 14, 8383–8397; f) J. D. Osborne, H. E. Randell-
Sly, G. S. Currie, A. R. Cowley, M. C. Willis, J. Am.
Chem. Soc. 2008, 130, 17232–17233; g) H. E. Randell-
Sly, J. D. Osborne, R. L. Woodward, G. S. Currie, M. C.
Willis, Tetrahedron 2009, 65, 5110–5117; h) C. Gon-
zµlez-Rodríguez, S. R. Parsons, A. L. Thompson, M. C.
Willis, Chem. Eur. J. 2010, 16, 10950–10954; i) R. J.
Pawley, G. L. Moxham, R. Dallanegra, A. B. Chaplin,
S. K. Brayshaw, A. S. Weller, M. C. Willis, Organome-
tallics 2010, 29, 1717–1728; j) C. Gonzµlez-Rodríguez,
R. J. Pawley, A. B. Chaplin, A. L. Thompson, A. S.
Weller, M. C. Willis, Angew. Chem. 2011, 123, 5240–
5244; Angew. Chem. Int. Ed. 2011, 50, 5134–5138.
[14] For intermolecular Rh-catalyzed hydroacylation of al-
kenes using non-chelating aldehydes, see: a) A. H. Roy,
C. P. Lenges, M. Brookhart, J. Am. Chem. Soc. 2007,
129, 2082–2093; b) K. Tanaka, Y. Shibata, T. Suda, Y.
Hagiwara, M. Hirano, Org. Lett. 2007, 9, 1215–1218;
c) Y. Shibata, K. Tanaka, J. Am. Chem. Soc. 2009, 131,
12552–12553; d) S. K. Murphy, A. Bruch, V. M. Dong,
Angew. Chem. Int. Ed. 2014, 53, 2455–2459; e) S. K.
Murphy, A. Bruch, V. M. Dong, Chem. Sci. 2015, 6,
174–180.
Gigler, F. E. Kühn, ACS Catal. 2012, 2, 613–621.
[6] a) Modern Rhodium-Catalyzed Organic Reactions,
(Ed.: A. P. Evans), Wiley-VCH, Weinheim, 2005; b) W.
Tang, X. Zhang, Chem. Rev. 2003, 103, 3029–3070; c) J.-
H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem. Soc. Rev. 2012,
41, 4126–4139; d) S. J. Roseblade, A. Pfaltz, Acc. Chem.
Res. 2007, 40, 1402–1411.
[7] a) Rhodium Catalyzed Hydroformylation, (Eds.:
P. W. N. M. van Leeuwen, C. Claver), Kluwer Academic
Publishers, Dordrecht, The Netherlands, 2000; b) C.
Claver, M. DiØguez, O. Pàmies, S. Castillón, Top. Orga-
nomet. Chem. 2006, 18, 35–64.
[8] M. C. Willis, Chem. Rev. 2010, 110, 725–748.
[9] For examples of hydroacylation reactions demonstrat-
ing a competitive decarbonylation pathway, see: a) K.
Sakai, J. Ide, O. Oda, N. Nakamura, Tetrahedron Lett.
1972, 13, 1287–1290; b) D. Milstein, J. Chem. Soc.
Chem. Commun. 1982, 1357–1358; c) D. Milstein, Orga-
nometallics 1982, 1, 1549–1551; d) S. H. Bergens, D. P.
Fairlie, B. Bosnich, Organometallics 1990, 9, 566–571.
[10] a) Z. Shen, H. A. Khan, V. M. Dong, J. Am. Chem.
Soc. 2008, 130, 2916–2917; b) Z. Shen, P. K. Dornan,
H. A. Khan, T. K. Woo, V. M. Dong, J. Am. Chem. Soc.
2009, 131, 1077–1091; c) H. A. Khan, K. G. M. Kou,
V. M. Dong, Chem. Sci. 2011, 2, 407–410.
[15] M. M. H. Khalil, F. A. Al-Seif, J. Coord. Chem. 2007,
60, 1191–1201.
[16] M. M. H. Khalil, F. A. Al-Seif, Res. Lett. Inorg. Chem.
2008, 1–4.
[11] K. G. M. Kou, D. N. Le, V. M. Dong, J. Am. Chem. Soc.
[17] For discussions on how bite angles affect reactivity, see:
a) P. W. N. M. van Leeuwen, P. C. J. Kamer, J. N. H.
Reek, Pure Appl. Chem. 1999, 71, 1443–1452; b) M.-N.
Birkholz (nØe Gensow), Z. Freixa, P. W. N. M. van
Leeuwen, Chem. Soc. Rev. 2009, 38, 1099–1118.
2014, 136, 9471–9476.
[12] For intermolecular Rh-catalyzed hydroacylation of al-
kenes using salicylaldehydes, see: a) M. Imai, M.
Tanaka, K. Tanaka, Y. Yamamoto, N. Imai-Ogata, M.
Shimowatari, S. Nagumo, N. Kawahara, H. Suemune, J.
Org. Chem. 2004, 69, 1144–1150; b) K. Tanaka, M.
Tanaka, H. Suemune, Tetrahedron Lett. 2005, 46, 6053–
6056; c) R. T. Stemmler, C. Bolm, Adv. Synth. Catal.
2007, 349, 1185–1198; d) Y. Inui, M. Tanaka, M. Imai,
K. Tanaka, H. Suemune, Chem. Pharm. Bull. 2009, 57,
1158–1160; e) M. M. Coulter, K. G. M. Kou, B. Galli-
gan, V. M. Dong, J. Am. Chem. Soc. 2010, 132, 16330–
16333; f) D. H. T. Phan, K. G. M. Kou, V. M. Dong, J.
Am. Chem. Soc. 2010, 132, 16354–16355; g) S. K.
Murphy, D. A. Petrone, M. M. Coulter, V. M. Dong,
Org. Lett. 2011, 13, 6216–6219; h) H.-J. Zhang, C.
Bolm, Org. Lett. 2011, 13, 3900–3903; i) S. K. Murphy,
M. M. Coulter, V. M. Dong, Chem. Sci. 2012, 3, 355–
358; j) M. von Delius, C. M. Le, V. M. Dong, J. Am.
Chem. Soc. 2012, 134, 15022–15032.
[13] For intermolecular Rh-catalyzed hydroacylation of al-
kenes using b-sulfur aldehydes, see: a) M. C. Willis, S. J.
McNally, P. J. Beswick, Angew. Chem. 2004, 116, 344–
347; Angew. Chem. Int. Ed. 2004, 43, 340–343; b) M. C.
Willis, H. E. Randell-Sly, R. L. Woodward, G. S. Currie,
Org. Lett. 2005, 7, 2249–2251; c) G. L. Moxham, H. E.
Randell-Sly, S. K. Brayshaw, R. L. Woodward, A. S.
Weller, M. C. Willis, Angew. Chem. 2006, 118, 7780–
7784; Angew. Chem. Int. Ed. 2006, 45, 7618–7622;
d) M. C. Willis, H. E. Randell-Sly, R. L. Woodward,
S. J. McNally, G. S. Currie, J. Org. Chem. 2006, 71,
5291–5297; e) G. L. Moxham, H. Randell-Sly, S. K.
[18] W. Leitner, M. Bühl, R. Fornika, C. Six, W. Baumann,
´
E. Dinjus, M. Kessler, C. Krüger, A. Rufinska, Organo-
metallics 1999, 18, 1196–1206.
[19] C. Kohrt, W. Baumann, A. Spannenberg, H.-J. Drexler,
I. D. Gridnev, D. Heller, Chem. Eur. J. 2013, 19, 7443–
7451. The X-ray crystallography data {CCDC 913096,
[Rh(dcpe)mac]BF4}
and
{CCDC
913098,
[Rh(dcpb)cod]BF4} were obtained from The Cam-
bridge Crystallographic Data Centre.
[20] C. Six, B. Gabor, H. Gçrls, R. Mynott, P. Philipps, W.
Leitner, Organometallics 1999, 18, 3316–3326. This bite
angle is obtained from an X-ray crystal structure of
[Ru(dcpp)(h3-C6H8)(h3-C6H8)].
[21] M. Daumas, Y. Vo-Quang, L. Vo-Quang, F. Le Goffic,
Synthesis 1989, 64–65. Systems that involve directing el-
ements on both coupling partners (i.e., a double-chela-
tion approach) have been found to be unreactive when
using catalysts modified with bidentate phosphine li-
gands (see ref.[12e]).
[22] L. McKinstry, T. Livinghouse, Tetrahedron 1995, 51,
7655–7666.
[23] a) N. Oohara, T. Imamoto, Bull. Chem. Soc. Jpn. 2002,
75, 1359–1365; b) T. Imamoto, K. Tamura, Z. Zhang, Y.
Horiuchi, M. Sugiya, K. Yoshida, A. Yanagisawa, I. D.
Gridnev, J. Am. Chem. Soc. 2012, 134, 1754–1769.
[24] M. D. Fryzuk, B. Bosnich, J. Am. Chem. Soc. 1977, 99,
6262–6267.
Adv. Synth. Catal. 2015, 357, 2233 – 2237
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