Efficient and selective nickel-catalyzed addition of H-P(O) and H-S bonds to alkynes

Li-Biao Han; Chen Zhang; Hideaki Yazawa; Shigeru Shimada

doi:10.1021/ja0494297

Efficient and selective nickel-catalyzed addition of H-P(O) and H-S bonds to alkynes

J Am Chem Soc. 2004 Apr 28;126(16):5080-1. doi: 10.1021/ja0494297.

Authors

Li-Biao Han¹, Chen Zhang, Hideaki Yazawa, Shigeru Shimada

Affiliation

¹ National Institute of Advanced Industrial Science and Technology, Tsukuba, Ibaraki, Japan. libiao-han@aist.go.jp

PMID: 15099086
DOI: 10.1021/ja0494297

Abstract

The cheap nickel catalysts are more reactive than the corresponding noble metal catalysts in the catalytic additions of a variety of P(O)-H bonds and an S-H bond to alkynes, affording regio- and stereoselectively both the Markovnikov and the anti-Markovnikov adducts, respectively, in high yields. A related five-coordinate hydrido nickel complex in the catalysis is successfully isolated, which can react readily with an alkyne to give the addition products.