Rhodium(iii)-catalyzed synthesis of phthalides by cascade addition and cyclization of benzimidates with aldehydes.
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.
Department of Chemistry, Yale University, Connecticut, 06520, USA.  jonathan.ellman@yale.edu ; Tel: +1-203-432-2647.
Yajing
Y
Lian
Robert G
RG
Bergman
Jonathan A
JA
Ellman