Secondary Benzylation with Benzyl Alcohols Catalyzed by A High-Valent Heterobimetallic Ir−Sn Complex

Susmita Podder, Joyanta Choudhury, and Sujit Roy*
Organometallics & Catalysis Laboratory, Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India sroy@chem.iitkgp.ernet.in
J. Org. Chem., 2007, 72 (8), pp 3129–3132
DOI: 10.1021/jo0625094
Publication Date (Web): March 17, 2007
Copyright © 2007 American Chemical Society
*

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

Abstract

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A highly efficient secondary benzylation procedure has been demonstrated using a high-valent heterobimetallic complex [Ir2(COD)2(SnCl3)2(Cl)2(μ-Cl)2] 1 as the catalyst in 1,2-dichloroethane to afford the corresponding benzylated products in moderate to excellent yields. The reaction was performed not only with carbon nucleophiles (arenes and heteroarenes) but also with oxygen (alcohol), nitrogen (amide and sulfonamide), and sulfur (thiol) nucleophiles. Mechanistic investigation showed the intermediacy of the ether in this reaction. An electrophilic mechanism is proposed from Hammett correlation.

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History

  • Published In Issue April 13, 2007
  • Received December 7, 2006

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