Journal of the American Chemical Society
COMMUNICATION
’ ACKNOWLEDGMENT
(11) (a) Cunico, R. F.; Maity, B. C. Org. Lett. 2002, 4, 4357. (b)
Cunico, R. F.; Pandey, R. K. J. Org. Chem. 2005, 70, 9048.
(12) Lindsay, C. M.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. 1
1988, 569.
(13) First-reported cross-coupling of a silane: (a) Hatanaka, Y.;
Hiyama, T. Tetrahedron Lett. 1988, 29, 97. Review: (b) Denmark, S. E.;
Sweis, R. F. Acc. Chem. Res. 2002, 35, 835 and ref therein. Example of
fluoride-free Hiyama couplings: (c) Hagiwara, E.; Gouda, K.; Hatanaka,
Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439.
(14) Though limited examples of the corresponding acylboron species
are known, to our knowledge they have not been employed as masked acyl
anion equivalents in cross-coupling reactions: (a) Yamashita, M.; Suzuki,
Y.; Segawa, Y.; Nozaki, K. J. Am. Chem. Soc. 2007, 129, 9570. (b)
Molander, G. A.; Raushel, J.; Ellis, N. M. J. Org. Chem. 2010, 75, 4304.
(15) Some leading references: (a) Linghu, X.; Johnson, J. S. Angew.
Chem., Int. Ed. 2003, 42, 2534. (b) Linghu, X.; Potnick, J. R.; Johnson,
J. S. J. Am. Chem. Soc. 2004, 126, 3070. (c) Linghu, X.; Bausch, C. C.;
Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 1833.
The authors dedicate this Communication to Prof. Dietmar
Seyferth. J.R.S. acknowledges the National Science Foundation
for support (NSF-GOALI 0848460). Dr. Matthew T. Tudge
(Merck & Co.) is thanked for assistance in the synthesis of PC1.
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dx.doi.org/10.1021/ja2064318 |J. Am. Chem. Soc. 2011, 133, 19574–19577