Work

Photoredox Generation of Carbon‐Centered Radicals Enables the Construction of 1,1‐Difluoroalkene Carbonyl Mimics

Year: 2017

Type: article

Abstract: Described is a facile, scalable route to access functional-group-rich gem-difluoroalkenes. Using visible-light-activated catalysts in conjunction with an arsenal of carbon-radical precursors, an array of trifluoromethyl-substituted alkenes undergoes radical defluorinative alkylation. Nonstabilized primary, secondary, and tertiary radicals can be used to install functional groups in a convergent manner, which would otherwise be challenging by two-electron pathways. The process readily extends to other perfluoroalkyl-substituted alkenes. In addition, we report the development of an organotrifluoroborate reagent to expedite the synthesis of the requisite trifluoromethyl-substituted alkene starting materials.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201709487

Authors: Simon B. Lang, Rebecca J. Wiles, Christopher B. Kelly, Gary A. Molander

Institution: University of Pennsylvania

Language: English

Topic: Radical Photochemical Reactions

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: Novel Borazines: Syntheses and Elaboration, A Novel Mechanistic Paradigm for Cross-Coupling, Purchase of a Mass Directed Liquid Chromatograph, Non-Organometallic Partners as Radical Precursors for the Diversification of Dual Catalytic Cross-Coupling Processes