Formal Insertion of Alkenes Into C(sp3)−F Bonds Mediated by Fluorine‐Hydrogen Bonding

Author:

Garg Arushi12ORCID,Gerwien Nils J.2ORCID,Fasting Carlo2,Charlton Alex1ORCID,Hopkinson Matthew N.12ORCID

Affiliation:

1. School of Natural and Environmental Sciences Newcastle University Bedson Building Newcastle upon Tyne NE1 7RU UK

2. Institut für Chemie und Biochemie Freie Universität Berlin Fabeckstrasse 34–36 14195 Berlin Germany

Abstract

AbstractC−F Insertion reactions represent an attractive approach to prepare valuable fluorinated compounds. The high strength of C−F bonds and the low reactivity of the fluoride released upon C−F bond cleavage, however, mean that examples of such processes are extremely scarce in the literature. Here we report a reaction system that overcomes these challenges using hydrogen bond donors that both activate C−F bonds and allow for downstream reactions with fluoride. In the presence of hexafluoroisopropanol, benzyl and propargyl fluorides undergo efficient formal C−F bond insertion across α‐fluorinated styrenes. This process, which does not require any additional fluorinating reagent, occurs under mild conditions and delivers products featuring the gem‐difluoro motif, which is attracting increasing interest in medicinal chemistry. Moreover, readily available organic bromides can be engaged directly in a one‐pot process that avoids the isolation of organic fluorides.

Funder

Deutsche Forschungsgemeinschaft

Verband der Chemischen Industrie

School of Natural and Environmental Sciences, Newcastle University

Publisher

Wiley

Subject

General Medicine

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