Work

Copper-Catalyzed C–H Fluorination/Functionalization Sequence Enabling Benzylic C–H Cross Coupling with Diverse Nucleophiles

Year: 2020

Type: article

Abstract: Site-selective transformation of benzylic C–H bonds into diverse functional groups is achieved via Cu-catalyzed C–H fluorination with N -fluorobenzenesulfonimide (NFSI), followed by substitution of the resulting fluoride with various nucleophiles. The benzyl fluorides generated in these reactions are reactive electrophiles in the presence of hydrogen-bond donors or Lewis acids, allowing them to be used without isolation in C–O, C–N, and C–C coupling reactions.

Source: Organic Letters

DOI: 10.1021/acs.orglett.0c02238

Authors: Aristidis Vasilopoulos, Dung L. Golden, Joshua A. Buss, Shannon S. Stahl

Institution: University of Wisconsin–Madison

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, National Institutes of Health, National Institute of General Medical Sciences

Awards: The Development of Enantioselective Nickel Catalysts for Late Stage Functionalization of Benzylic C–H Bonds, Acquisition of a 400 MHz NMR Spectrometer for Chemical Research and Learning, Radical Relay Methods for Selective C-H Oxidation, QExactive (Orbitrap) mass spectrometer, Catalytic Redox Reactions for Pharmaceutical Synthesis