Synlett 2017; 28(14): 1707-1714
DOI: 10.1055/s-0036-1590888
cluster
© Georg Thieme Verlag Stuttgart · New York

Visible-Light-Mediated Synthesis of Pyrazines from Vinyl Azides Utilizing a Photocascade Process

Asik Hossain, Santosh K. Pagire, Oliver Reiser*
This work was supported by the German Science Foundation (DFG) (GRK 1626, Chemical Photocatalysis)
Further Information

Publication History

Received: 30 June 2017

Accepted after revision: 09 August 2017

Publication Date:
16 August 2017 (eFirst)

Dedicated to Professor Albert Padwa on the occasion of his 80th birthday

Published as part of the ISHC Conference Special Section

Abstract

A convenient method for the synthesis of substituted pyrazines from vinyl azides has been developed. This method is enabled by a dual-energy and electron-transfer strategy by visible-light photocatalysis. Initially, vinyl azides are activated by a triplet sensitization process from an excited ruthenium photocatalyst in the presence of water to form dihydropyrazines, followed by a single-electron-transfer (SET) process under oxygen (air) atmosphere that leads to the tetrasubstituted pyrazines in good to excellent yields.

Supporting Information