Conjugated 1,3-enynes are common structural motifs in natural products, biologically active compounds and various organic molecules and therefore interesting synthetic targets. Direct dimerization of terminal alkynes to form conjugated 1,3 enynes is most efficient and economical. We have shown that “Inverse” FLPs composed of Verkade’s superbase and moderate to weak Lewis acids such as 9-BBN and BPh3 are capable of selectively deprotonating terminal alkynes. However, only binuclear Lewis acid base complexes of formula (C6F5)3Al-P(N(R)CH2CH2)3N-Al(C6F5)3 derived from reactions of the strong Lewis acid Al(C6F5)3 with various substituted Verkade bases proved to be efficient in catalysing the dimerization of terminal alkynes to gem-enynes.

Catalytic dimerization of terminal alkynes to gem-enynes using a binuclear Lewis acid–base complex

2019 Fall National Meeting

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