Double Heteroatom Functionalization of Arenes Using Benzyne Three-Component Coupling


Garcia-Lopez J., Cetin M., Greaney M. F.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol.54, no.7, pp.2156-2159, 2015 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 54 Issue: 7
  • Publication Date: 2015
  • Doi Number: 10.1002/anie.201410751
  • Journal Name: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2156-2159
  • Bursa Uludag University Affiliated: Yes

Abstract

Arynes participate in three-component coupling reactions with N, S, P, and Se functionalities to yield 1,2-heteroatom-difunctionalized arenes. Using 2-iodophenyl aryl-sulfonates as benzyne precursors, we could effectively add magnesiated S-, Se-, and N-nucleophilic components to the strained triple bond. In the same pot, addition of electrophilic N, S, or P reagents and a copper(I) catalyst trapped the intermediate aryl Grignard to produce a variety of 1,2-difunctionalized arenes.