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Doyle‐Kirmse Rearrangement Reactions of Difluoroacetates
Author(s) -
Jana Sripati,
Koenigs Rene M.
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900099
Subject(s) - chemistry , carbene , allylic rearrangement , rhodium , yield (engineering) , catalysis , cope rearrangement , rearrangement reaction , combinatorial chemistry , photochemistry , nanotechnology , organic chemistry , materials science , metallurgy
In this report, we describe an application of ethyl difluoroacetate‐substituted allylic sulfides in Doyle‐Kirmse rearrangement reactions that allow efficient access to valuable fluorinated small molecules with applications in total synthesis and drug discovery. A cheap and readily available rhodium catalyst or – in a metal‐free variant – visible light was used to generate a carbene intermediate to access rearrangement reactions in high yield.