Synthesis 2017; 49(18): 4124-4132
DOI: 10.1055/s-0036-1590855
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© Georg Thieme Verlag Stuttgart · New York

Vinylation of Iododifluoromethylated Alcohols via a Light-Promoted Intramolecular Atom-Transfer Reaction

Liubov I. Panferova, Marina I. Struchkova, Alexander D. Dilman*
  • N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation   Email: adil25@mail.ru
This work was supported by the Russian Science Foundation (project 17-13-01041).
Further Information

Publication History

Received: 16 May 2017

Accepted after revision: 06 July 2017

Publication Date:
07 August 2017 (eFirst)

Abstract

A method for the synthesis of gem-difluorohomoallylic alcohols by the substitution of iodine in the iododifluoromethyl group by a vinyl fragment is described. The reaction proceeds via an intramolecular iodine atom transfer followed by β-elimination. The reaction is performed in the presence of an iridium photocatalyst, fac-Ir(ppy)3, and triphenylphosphine under irradiation with light-emitting diodes.

Supporting Information

 
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