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Synlett 2008(14): 2127-2131  
DOI: 10.1055/s-2008-1078242
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Reduction of Aryl Iodides Using 4-DMAP Methiodide Salt

Jean Garniera, John A. Murphy*a, Sheng-Ze Zhoua, Andrew T. Turnerb
a WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, UK
b UM4 Main Lb Block Process R&D, AstraZeneca, Hurdsfield Industrial Estate, Macclesfield, SK10 2NA, UK
Fax: +44(141)5484822; e-Mail: John.Murphy@strath.ac.uk;
Further Information

Publication History

Received 2 June 2008
Publication Date:
31 July 2008 (online)

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Abstract

An efficient one-pot procedure is described for the reduction of aryl iodides to aryl anions using a structurally simple bis-pyridinylidene electron donor, prepared in situ by treating 4-DMAP methiodide salt with base. The results show (i) that pyridinylidene carbenes can be easily used for intermolecular C-C bond formation, (ii) that bis-pyridinylidenes demonstrate superior robustness compared to electron-donor systems based on bis-imidazolylidenes, and (iii) that electron-donor strength is enhanced in the simplified DMAP-based donor. Deuterated analogues of this donor also provide mechanistic information on the source of protons when the aryl anions are quenched in situ.

Key words

electron donor - pyridinylidene - reduction - 4-DMAP

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