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Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4-Dioxane.

ABSTRACT: 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.

SUBMITTER: Hokamp T

PROVIDER: S-EPMC5698765 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4-Dioxane.

Hokamp Tobias T Dewanji Abhishek A Lübbesmeyer Maximilian M Mück-Lichtenfeld Christian C Würthwein Ernst-Ulrich EU Studer Armido A

Angewandte Chemie (International ed. in English) 20170919 43

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. ...[more]

PMID: 28841248

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