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Regioconvergent Nucleophilic Substitutions with Morita-Baylis-Hillman Fluorides.

ABSTRACT: Lithium iodide enables regioconvergent C-F bond functionalization of isomeric Morita-Baylis-Hillman fluorides with carbon, sulfur, and nitrogen nucleophiles. The defluorinative carbon-carbon and carbon-heteroatom bond formations give multifunctional compounds in excellent yields and with good to high diastereoselectivities at room temperature. The possibility of catalytic enantioselective allylation is also discussed.

SUBMITTER: Formen JSSK

PROVIDER: S-EPMC11301663 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Regioconvergent Nucleophilic Substitutions with Morita-Baylis-Hillman Fluorides.

Formen Jeffrey S S K JSSK Lynch Ciarán C CC Nelson Eryn E Yuan Andi A Steber Sarah E SE Wolf Christian C

The Journal of organic chemistry 20240716 15

Lithium iodide enables regioconvergent C-F bond functionalization of isomeric Morita-Baylis-Hillman fluorides with carbon, sulfur, and nitrogen nucleophiles. The defluorinative carbon-carbon and carbon-heteroatom bond formations give multifunctional compounds in excellent yields and with good to high diastereoselectivities at room temperature. The possibility of catalytic enantioselective allylation is also discussed. ...[more]

PMID: 39014960

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