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Paper | Regular issue | Vol 32, No. 5, 1991, pp.949-963
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5698
Cobalt-mediated Alkylation of Siloxy Furans

John G. Stuart and Kenneth M. Nicholas*

*Department of Chemistry and Biochemistry, University of Oklahoma, Nrman, Oklahoma 73019, U.S.A.

Abstract

Dicobalt hexacarbonyl complexes of propargylium and α-vinylpropargylium cations couple efficiently with 2-trimethylsilyloxyfuran (5), 4-trimethylsilyloxy-2-benzyloxymethylfuran (15) and 2-trimethylsilyl-3-trimethylsilyloxy-4-ethylbenzo[b]furan (20) to produce the corresponding complexed furan derivatives in good yields. A convenient procedure for introducing the 2,4-enyne moiety regio- and stereoselectively into the above heterocycles using this methodology is described.