4.4 Article

2-Aryl propionamides via 1,4-aryl radical migration from N-arylsulfonyl-2-bromopropionamides

Journal

TETRAHEDRON LETTERS
Volume 50, Issue 46, Pages 6311-6314

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.08.125

Keywords

Copper; ATRC; Atom transfer; Radical; Aryl migration; Dimethylpiperazine

Funding

  1. EPSRC

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Reaction of N-alkyl-N-arylsulfonyl-2-halo-propionamides with pentamethyldiethylenetriamine and either CuBr or CuCl leads to 2-aryl propionamides via initial radical generation, 1,4-aryl migration with loss of SO2 and reduction of the intermediate amidyl radical in 40-99% yields. (C) 2009 Elsevier Ltd. All rights reserved.

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