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Chem Sci. 2012 Jan 1;3(10):3088-3092. Epub 2012 Aug 2.

Rhodium(iii)-catalyzed synthesis of phthalides by cascade addition and cyclization of benzimidates with aldehydes.

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1
Department of Chemistry, Yale University, Connecticut, 06520, USA. jonathan.ellman@yale.edu ; Tel: +1-203-432-2647.

Abstract

We herein report the Rh(iii)-catalyzed C-H bond activation and addition of benzimidates to aldehydes to afford biologically important phthalides in a single step. The imidate is a novel and unexplored directing group that not only enables C-H bond activation and addition to aldehydes, but also serves to capture the reversibly formed alcohol intermediate. The reaction shows broad scope with a high level of functional group compatibility and is applicable to both aromatic and aliphatic aldehydes.

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