Work

Fluorinated alcohols: powerful promoters for ring-opening reactions of epoxides with carbon nucleophiles

Year: 2021

Type: article

Abstract: Ring-opening reactions of epoxides with carbon nucleophiles are valuable transformations for constructing functionalized carbon-carbon bonds.Epoxide ring-opening methods typically require Lewis acidic additives and/or strong nucleophiles to overcome the activation barrier for these reactions.Fluorinated alcohol solvents present a desirable alternative, enhancing the efficacy of these reactions with weak and neutral carbon nucleophiles by promoting electrophilic activation of the epoxide.We present here a thorough review of the literature regarding epoxide ring-opening reactions with carbon nucleophiles in fluorinated alcohol solvents, concluding with a few recent examples with aziridines.

Source: ARKIVOC

DOI: 10.24820/ark.5550190.p011.449

Authors: Taylor L. Dover, Frank E. McDonald

Institutions: Northwestern University, Emory University, Yale University, Stanford University

Language: English

Topic: Physical Organic Chemistry and Reaction Kinetics

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Science Foundation, Emory University, Japan Society for the Promotion of Science

Award: G6671297155