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Radical Hydrodeiodination of Aryl, Alkenyl, Alkynyl, and Alkyl Iodides with an Alcoholate as Organic Chain Reductant through Electron Catalysis
Author(s) -
Dewanji Abhishek,
MückLichtenfeld Christian,
Studer Armido
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201601930
Subject(s) - chemistry , aryl , reagent , alkyl , iodide , catalysis , organic chemistry , medicinal chemistry , combinatorial chemistry
A simple and efficient method for radical hydrodeiodination is reported. The novel approach uses electron catalysis. In situ generated Na‐alcoholates are introduced as radical chain reducing reagents and reactions work with O 2 as cheap initiator. Hydrodeiodination works on aryl, alkenyl, alkynyl iodides and a tert‐alkyl iodide also gets reduced applying the method. Albeit less general, the method is also applicable to the reduction of aryl bromides. The novel reagent is successfully used to conduct typical reductive radical cyclization reactions and mechanistic studies are reported.