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

Andrew J. Clark; Stuart R. Coles; Alana E.C. Collis; David R. Fullaway; Nicholas P. Murphy; Paul Wilson

doi:10.1016/j.tetlet.2009.08.125

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

Andrew J. Clark, Stuart R. Coles, Alana E.C. Collis, David R. Fullaway, Nicholas P. Murphy, Paul Wilson

Research output: Contribution to journal › Article › Research › peer-review

16 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	6311-6314
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	46
DOIs	https://doi.org/10.1016/j.tetlet.2009.08.125
Publication status	Published - 18 Nov 2009
Externally published	Yes

Keywords

Aryl migration
Atom transfer
ATRC
Copper
Dimethylpiperazine
Radical

Access to Document

10.1016/j.tetlet.2009.08.125

Link to publication in Scopus

Cite this

Clark, A. J., Coles, S. R., Collis, A. E. C., Fullaway, D. R., Murphy, N. P., & Wilson, P. (2009). 2-Aryl propionamides via 1,4-aryl radical migration from N-arylsulfonyl-2-bromopropionamides. Tetrahedron Letters, 50(46), 6311-6314. https://doi.org/10.1016/j.tetlet.2009.08.125

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AU - Coles, Stuart R.

AU - Collis, Alana E.C.

AU - Fullaway, David R.

AU - Murphy, Nicholas P.

AU - Wilson, Paul

PY - 2009/11/18

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AB - 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.

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KW - Atom transfer

KW - ATRC

KW - Copper

KW - Dimethylpiperazine

KW - Radical

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