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

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.

SUBMITTER: Lian Y

PROVIDER: S-EPMC3462028 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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

Lian Yajing Y Bergman Robert G RG Ellman Jonathan A JA

Chemical science 20120101 10

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. ...[more]

PMID: 23050074

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