Addition reactions of heteroatom-COX (X = OR, NR2, COOR) species with alkynes

Abstract

Heteroatom-COX species where the heteroatom is Cl, S, or Sn and X is alkoxy, amino, or alkoxycarbonyl group were found to add to the triple bond of alkynes regio- and stereoselectively in the presence of Rh, Pd, or Ni catalyst. Scope and limitation of these synthetic reactions were disclosed. Mechanistic study revealed that oxidative addition of these heteroatom-COX bonds readily took place and the resulting adducts were isolable and characterized by X-ray diffraction analysis. Synthetic applications of the catalytic reactions were also demonstrated.