Photochemical, Metal-Free Sigmatropic Rearrangement Reactions of Sulfur Ylides

Chemistry : a European Journal
Zhen YangRene M Koenigs

Abstract

Sigmatropic rearrangement reactions constitute one of the most fundamental reactions of carbenes. While state-of-the-art synthetic methods require the use of expensive precious metal catalysts, the application of visible light for the photolysis of α-aryldiazoacetates is much less investigated and provides an operationally simple entry to carbenes under mild reaction conditions. Herein, we report on blue-light induced sigmatropic rearrangement reactions of sulfur compounds with α-aryldiazoacetates. This process, depending on the substitution pattern of the sulfide, opens up formal insertion reactions of carbenes into S-N, S-C, or C-H bonds.

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Citations

Apr 9, 2019·Chemical Communications : Chem Comm·Feifei He, Rene M Koenigs
Jul 2, 2019·Chemical Communications : Chem Comm·Zhen YangRene M Koenigs
Oct 10, 2019·Chemical Communications : Chem Comm·Sripati JanaRene M Koenigs
Dec 12, 2019·Chemistry : a European Journal·Sripati JanaRene M Koenigs
Jan 31, 2020·Chemistry : a European Journal·Amanda F da SilvaIgor D Jurberg
May 20, 2020·Chemistry, an Asian Journal·Yingying XuYong Wu
Aug 6, 2020·Chemistry : a European Journal·Sripati JanaRene M Koenigs
May 7, 2021·Journal of the American Chemical Society·Leona L RodriguesChristopher Barner-Kowollik

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