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Direct transition-metal-free intramolecular arylation of phenols.

ABSTRACT: Direct transition-metal-free, base-mediated intramolecular arylation of phenols with aryl halides has been developed. In the presence of 2.5 equiv of t-BuOK in dioxane at 140 degrees C, the intramolecular cyclization of 3-(2-halobenzyloxy)phenols affords 6H-benzo[c]chromenes in high yields. This reaction proceeds by an initial formation of a benzyne intermediate followed by an aromatic sp(2) C-H functionalization (a formal C-H activation) to form the carbon-carbon bond.

SUBMITTER: Bajracharya GB 

PROVIDER: S-EPMC2627406 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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Direct transition-metal-free intramolecular arylation of phenols.

Bajracharya Gan B GB   Daugulis Olafs O  

Organic letters 20080918 20

Direct transition-metal-free, base-mediated intramolecular arylation of phenols with aryl halides has been developed. In the presence of 2.5 equiv of t-BuOK in dioxane at 140 degrees C, the intramolecular cyclization of 3-(2-halobenzyloxy)phenols affords 6H-benzo[c]chromenes in high yields. This reaction proceeds by an initial formation of a benzyne intermediate followed by an aromatic sp(2) C-H functionalization (a formal C-H activation) to form the carbon-carbon bond. ...[more]

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