A Water-Soluble Rhenium(I) Catalyst for the Regio- and Stereoselective C(sp2)-H Alkenylation of N-Pyridyl-/N-Pyrimidylindole and the N-H Alkenylation of N-Pyrimidylaniline Derivatives with Ynamides.

Abstract

A water-soluble and low-valent rhenium(I) catalyst for the C2 alkenylation of N-pyridyl/N-pyrimidylindole derivatives with ynamides under mild conditions using water as the solvent has been described. The reaction of N-pyridyl/N-pyrimidyl indole with the ynamide afforded the C2-Z-selective alkenylation derivative as the sole product, and the reactions of N-pyrimidylanilines delivered the corresponding N-alkenylated product rather than the expected C-H alkenylation products in high yields under the same conditions.