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Cs₂CO₃-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones.

ABSTRACT: The reaction of bromopropargylic alcohols with phenols in the presence of Cs₂CO₃/DMF affords α-phenoxy-α'-hydroxyketones (1:1 adducts) and α,α-diphenoxyketones (1:2 adducts) in up to 92% and 24% yields, respectively. Both products are formed via ring opening of the same intermediates, 1,3-dioxolan-2-ones, generated in situ from bromopropargylic alcohols and Cs₂CO₃.

SUBMITTER: Volostnykh OG

PROVIDER: S-EPMC9039521 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature

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Cs2CO3-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones.

Volostnykh Ol'ga G OG Shemyakina Olesya A OA Stepanov Anton V AV Ushakov Igor' A IA

Beilstein journal of organic chemistry 20220412

The reaction of bromopropargylic alcohols with phenols in the presence of Cs2CO3/DMF affords α-phenoxy-α'-hydroxyketones (1:1 adducts) and α,α-diphenoxyketones (1:2 adducts) in up to 92% and 24% yields, respectively. Both products are formed via ring opening of the same intermediates, 1,3-dioxolan-2-ones, generated in situ from bromopropargylic alcohols and Cs2CO3. ...[more]

PMID: 35529892

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