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

Mahesh, Mohan and Murphy, J.A. and LeStrat, Franck and Wessel, Hans Peter (2009) Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): Efficient formation of products derived from aryl radicals. Beilstein Journal of Organic Chemistry, 5 (1). ISSN 1860-5397 (http://dx.doi.org/10.3762/bjoc.5.1)

Abstract

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.

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  Item type:	Article
  ID code:	19256
  Dates:	Date Event 12 January 2009 Published
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Strathprints Administrator
  Date deposited:	22 Oct 2010 09:23
  Last modified:	11 Nov 2024 09:24
  URI:	https://strathprints.strath.ac.uk/id/eprint/19256