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Rhodium(III)-catalyzed indazole synthesis by C-H bond functionalization and cyclative capture.

ABSTRACT: An efficient, one-step, and highly functional group-compatible synthesis of substituted N-aryl-2H-indazoles is reported via the rhodium(III)-catalyzed C-H bond addition of azobenzenes to aldehydes. The regioselective coupling of unsymmetrical azobenzenes was further demonstrated and led to the development of a new removable aryl group that allows for the preparation of indazoles without N-substitution. The 2-aryl-2H-indazole products also represent a new class of readily prepared fluorophores for which initial spectroscopic characterization has been performed.

SUBMITTER: Lian Y

PROVIDER: S-EPMC3656829 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

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Rhodium(III)-catalyzed indazole synthesis by C-H bond functionalization and cyclative capture.

Lian Yajing Y Bergman Robert G RG Lavis Luke D LD Ellman Jonathan A JA

Journal of the American Chemical Society 20130503 19

An efficient, one-step, and highly functional group-compatible synthesis of substituted N-aryl-2H-indazoles is reported via the rhodium(III)-catalyzed C-H bond addition of azobenzenes to aldehydes. The regioselective coupling of unsymmetrical azobenzenes was further demonstrated and led to the development of a new removable aryl group that allows for the preparation of indazoles without N-substitution. The 2-aryl-2H-indazole products also represent a new class of readily prepared fluorophores fo ...[more]

PMID: 23642256

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