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Direct Substitution of Hydroxy Group of π-Activated Alcohols with Electron-Deficient Amines Using Re2O7 Catalyst

Braja Gopal Das, Rajender Nallagonda and Prasanta Ghorai*

*Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal-462023, India, Email: pghoraiiiserb.ac.in

B. G. Das, R. Nallagonda, P. Ghorai, J. Org. Chem., 2012, 77, 5577-5583.

DOI: 10.1021/jo300706b (free Supporting Information)


Abstract

A simple Re2O7-catalyzed direct dehydrative coupling between π-activated alcohols with electron-deficient amines has been achieved under mild and open flask conditions. The protocol alows the conversion of allylic, benzylic, and propargylic alcohols. The mechanistic proof for the SN1-type process has also been provided.

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Key Words

Allylic Amines, Propargylic Amines, Benzylic Amines


ID: J42-Y2012-2090