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
N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation   eMail: adil25@mail.ru
,
Marina I. Struchkova
N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation   eMail: adil25@mail.ru
,
N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation   eMail: adil25@mail.ru
› Institutsangaben
This work was supported by the Russian Science Foundation (project 17-13-01041).
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Publikationsverlauf

Received: 16. Mai 2017

Accepted after revision: 06. Juli 2017

Publikationsdatum:
07. August 2017 (online)


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.

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