Low‐valent indium(I)‐mediated nickel‐catalyzed propargylation of aldehydes is described. The nickel/indium(I)‐mediated reaction of propargylic carbonates possessing different substitution patterns afforded syn‐homopropargylic alcohols in high yields upon coupling with a variety of carbonyl compounds. Both the nickel catalyst and the phosphane ligands were found to play a crucial role in this transformation. The diastereoselectivity is strongly dependent on the ligand employed. A mechanism involving umpolung of the propargylnickel intermediates under the influence of low‐valent indium is proposed to account for the dependence of the stereochemical characteristics of the phosphane ligands.
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Hirashita et al. (2012) studied this question.
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