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 Eur.

Nickel-Catalyzed Indium(I)-Mediated syn-Selective Propargylation of Aldehydes. -The Ni-catalyzed InI-mediated propargylation of carbonyl compounds gives the corresponding homopropargylic alcohols in high yields with syn selectivity. This stereoselectivity is opposite to In(0)-mediated or Pd-catalyzed InI-mediated reactions. -(HIRASHITA*, T.; SUZUKI, Y.; TSUJI, H.; SATO, Y.; NAITO, K.; ARAKI, S.; Eur. J. Org. Chem. 2012, 29, 5668-5672, http://dx.