Highly Selective Markovnikov Addition of Hypervalent H-Spirophosphoranes to Alkynes Mediated by Palladium Acetate: Generality and Mechanism

LB Han, Y Ono, Q Xu, S Shimada

Index: Han, Li-Biao; Ono, Yutaka; Xu, Qing; Shimada, Shigeru Bulletin of the Chemical Society of Japan, 2010 , vol. 83, # 9 p. 1086 - 1099

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Citation Number: 10

Abstract

Palladium acetate efficiently catalyzes the addition of an H-spirophosphorane (pinacolato) 2 PH to alkynes to give Markovnikov addition products highly selectively. The addition products can be easily converted to the corresponding alkenylphosphonates and phosphonic acids via simple hydrolysis or thermal decomposition. This new reaction is a general method for the introduction of phosphorus functionality to the internal carbons of ...