4 Cross-Dehydrogenative Coupling Involving Alkynes for C(sp²)—C(sp) Bond Formation

Abstract

Cross-dehydrogenative coupling reactions represent one of the most environmentally friendly and atom-economic strategies to achieve carbon–carbon or carbon–heteroatom bond formation from non-prefunctionalized substrates, formally producing only dihydrogen as waste. Using terminal alkynes as one of the coupling partners in cross-dehydrogenative couplings, the sustainable synthesis of a myriad of alkynylated compounds is possible. In this review, the major advances in cross-dehydrogenative couplings involving alkynes are covered, with a focus on the formation of C(sp²)—C(sp) bonds, leading to alkynylated arenes, 1,3-enynes, and ynone derivatives. Synthetic strategies, reaction conditions, and the scope of each method are critically discussed, from early developments to date.

Key words

cross-dehydrogenative coupling - transition-metal catalysis - alkynes - cross coupling - alkynylation - C—H activation - radical chemistry - C—C bond formation - heterocycles - carbonyl compounds - aromatic compounds - 1,3-enynes

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