Visible-Light-Induced [4+2] Annulation of Thiophenes and Alkynes to Construct Benzene Rings

Angew Chem Int Ed Engl. 2019 Aug 26;58(35):12206-12210. doi: 10.1002/anie.201905971. Epub 2019 Jul 25.

Abstract

The [4+2] annulation represents an elegant and versatile synthetic protocol for the construction of benzene rings. Herein, a strategy for visible-light induced [4+2] annulation of thiophenes and alkynes, to afford benzene rings, is presented. Under simple and mild reaction conditions, the ready availability and structural diversity of thiophenes and alkynes permit the facile synthesis of several substituted aromatic rings. Valuable drugs and amino acids are also well tolerated. Moreover, DFT calculations explain the high regioselectivity of the reaction.

Keywords: alkynes; annulations; photochemistry; radicals; thiophenes.

Publication types

  • Research Support, Non-U.S. Gov't