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Efficient Solvent-Free Selective Monoalkylation of Arylacetonitriles with Mono-, Bis-, and Tris-primary Alcohols Catalyzed by a Cp*Ir Complex

Supporting Info

Christian Löfberg,^† Ronald Grigg,*^† Mark A. Whittaker,^† Ann Keep,^‡ and Andrew Derrick^§

Molecular, Innovation, Diversity, and Automated Synthesis (MIDAS) Centre, Department of Chemistry, University of Leeds, LS2 9JT, United Kingdom, Johnson Matthey, Orchard Road, Royston, Hertz, SG8 5HE, United Kingdom, and Pfizer, Ramsgate Road, Sandwich, Kent, CT13 9NJ, United Kingdom

J. Org. Chem., 2006, 71 (21), pp 8023–8027

DOI: 10.1021/jo061113p

Publication Date (Web): September 9, 2006

†

University of Leeds.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

‡

Johnson Matthey.

Pfizer.(1) Reviews: (a) Alcaide, B.; Almendros, P. Eur. J. Org. Chem. 2002, 1595. (b) List, B. Tetrahedron 2002, 58, 5573.

, r.grigg@leeds.ac.uk

Abstract

Our objectives were to develop catalytic atom-economic processes accessing and/or incorporating versatile functionality using aryl/heteroaryl acetonitriles as substrates. We report essentially solvent-free [Cp*IrCl₂]₂ catalyzed redox neutral processes whereby substituted acetonitriles react with primary alcohols to deliver monosubstituted aryl/heteroaryl acetonitriles in excellent yield. We further demonstrate that such processes can be achieved by conventional or microwave heating and that bis- and tris-primary alcohols are also processed efficiently.

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Published In Issue October 13, 2006
Received May 31, 2006

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Article

Efficient Solvent-Free Selective Monoalkylation of Arylacetonitriles with Mono-, Bis-, and Tris-primary Alcohols Catalyzed by a Cp*Ir Complex