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

Index: J. Am. Chem. Soc. 126 , 5080, (2004)

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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.