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Iron‐Catalyzed Carbenoid‐Transfer Reactions of Vinyl Sulfoxonium Ylides: An Experimental and Computational Study
Author(s) -
Vaitla Janakiram,
Bayer Annette,
Hopmann Kathrin H.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201810451
Subject(s) - carbenoid , catalysis , chemistry , substrate (aquarium) , scope (computer science) , computational chemistry , combinatorial chemistry , organic chemistry , rhodium , computer science , geology , oceanography , programming language
A method for the generation of unprecedented vinyl carbenoids from sulfoxonium ylides has been developed and applied in the synthesis of a diverse array of heterocycles such as indolizines, pyrroles, 3‐pyrrolin‐2‐ones, and furans. The reactions proceed by FeBr 2 catalysis under mild reaction conditions with a broad substrate scope. A reaction pathway involving iron carbenoids is proposed based on a series of control experiments and DFT calculations.