Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): efficient formation of products derived from aryl radicals

Tetrakis(dimethylamino)ethylene (TDAE 1), has been exploited for the first time as a mild reagent for the reduction of arenediazonium salts to aryl radical intermediates through a single electron transfer (SET) pathway. Cyclization of the aryl radicals produced in this way led, in appropriate substr...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2009-01, Vol.5 (1), p.1-1
Main Authors: Mahesh, Mohan, Murphy, John A, LeStrat, Franck, Wessel, Hans Peter
Format: Article
Language:English
Subjects:
Chemistry
cyclization
electron transfer
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indole
indoline
radical
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Summary:Tetrakis(dimethylamino)ethylene (TDAE 1), has been exploited for the first time as a mild reagent for the reduction of arenediazonium salts to aryl radical intermediates through a single electron transfer (SET) pathway. Cyclization of the aryl radicals produced in this way led, in appropriate substrates, to syntheses of indolines and indoles. Cascade radical cyclizations of aryl radicals derived from arenediazonium salts are also reported. The relative ease of removal of the oxidized by-products of TDAE from the reaction mixture makes the methodology synthetically attractive.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.5.1