Synthesis 2018; 50(15): 2930-2935
DOI: 10.1055/s-0036-1591583
special topic
© Georg Thieme Verlag Stuttgart · New York

Dimerization of Benzyl and Allyl Halides via Photoredox-Mediated Disproportionation of Organozinc Reagents

Vitalij V. Levin
a  N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation
,
Daniil P. Agababyan
a  N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation
b  D. Mendeleev University of Chemical Technology of Russia, Higher Chemical College, Miusskaya sq. 9, 125047 Moscow, Russian Federation   Email: adil25@mail.ru
,
Marina I. Struchkova
a  N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation
,
a  N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation
› Author Affiliations
This work was supported by the Russian Foundation for Basic Research (project 16-29-10661).
Further Information

Publication History

Received: 01 February 2018

Accepted after revision: 09 April 2018

Publication Date:
23 May 2018 (online)

Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

Benzyl and allyl halides undergo homocoupling when treated with zinc in the presence of a catalytic amount of a cationic iridium(III) complex under irradiation with 400 nm light-emitting diodes. The reaction proceeds through the intermediate formation of an organozinc reagent, which disproportionates to a free radical and elemental zinc under photoredox conditions.

 
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