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Synthesis of 2,3-Dihydrobenzofurans via the Palladium Catalyzed Carboalkoxylation of 2-Allylphenols.

ABSTRACT: A new Pd-catalyzed alkene carboalkoxylation strategy for the preparation of 2,3-dihydrobenzofurans is described. This method effects the coupling of readily available 2-allylphenol derivatives with aryl triflates to generate a wide range of functionalized 2,3-dihydrobenzofurans in good yields and diastereoselectivities (up to >20:1). Use of newly developed reaction conditions that promote anti-heteropalladation of the alkene is essential in order to generate products in high yield.

SUBMITTER: Hutt JT

PROVIDER: S-EPMC5382964 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Synthesis of 2,3-Dihydrobenzofurans via the Palladium Catalyzed Carboalkoxylation of 2-Allylphenols.

Hutt Johnathon T JT Wolfe John P JP

Organic chemistry frontiers : an international journal of organic chemistry 20160822 10

A new Pd-catalyzed alkene carboalkoxylation strategy for the preparation of 2,3-dihydrobenzofurans is described. This method effects the coupling of readily available 2-allylphenol derivatives with aryl triflates to generate a wide range of functionalized 2,3-dihydrobenzofurans in good yields and diastereoselectivities (up to >20:1). Use of newly developed reaction conditions that promote <i>anti</i>-heteropalladation of the alkene is essential in order to generate products in high yield. ...[more]

PMID: 28392926

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