Nicholas Reaction

R. F. Lockwood, K. M. Nicholas, Tetrahedron Letters 1977, 4163.

The reaction of dicobalthexacarbonyl-stabilized propargyl cations with nucleophiles, followed by oxidative demetalation to yield propargylated products:

Stereochemistry: S. L. Schreiber et al., J. Am. Chem. Soc. 109, 5749 (1987); A. V. Muehldorf et al., Tetrahedron Letters 35, 8755 (1994). Scope and limitations: K. D. Roth, Synlett 1992, 435; K. D. Roth, U. Müller, Tetrahedron Letters 34, 2919 (1993). Synthetic applications: P. A. Jacobi, W. Zheng, ibid. 2581, 2585; E. Tyrrell et al., Synlett 1993, 769. Diastereoselective applications: J. Berge et al., Tetrahedron Letters 38, 685 (1997); A. Mann et al., J. Chem. Soc. Perkin Trans. I 1998, 1427. Enantioselective applications: S. Tanaka et al., Tetrahedron 50, 12883 (1994); A. M. Montana et al., Tetrahedron Letters 40, 6499 (1999). Review: K. M. Nicholas, Accts. Chem. Res. 20, 207-214 (1987).