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Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4‐Dioxane
Author(s) -
Hokamp Tobias,
Dewanji Abhishek,
Lübbesmeyer Maximilian,
MückLichtenfeld Christian,
Würthwein ErnstUlrich,
Studer Armido
Publication year - 2017
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.201706534
Subject(s) - chemistry , aryl , reagent , catalysis , sodium hydride , hydride , phenanthroline , aryl radical , medicinal chemistry , organic chemistry , alkyl , metal
A practical method for radical chain reduction of various aryl bromides and chlorides is introduced. The thermal process uses NaH and 1,4‐dioxane as reagents and 1,10‐phenanthroline as an initiator. Hydrodehalogenation can be combined with typical cyclization reactions, proving the nature of the radical mechanism. These chain reactions proceed by electron catalysis. DFT calculations and mechanistic studies support the suggested mechanism.