Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper-N-Heterocyclic Carbene Complex

• Published in: Angewandte Chemie International Edition Vol. 54; no. 46; pp. 13734 - 13738
• Main Authors: Cheng, Li-Jie, Cordier, Christopher J.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 09.11.2015; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: alkynes; carbene ligands; Carbenes; Catalysis; Catalysts; Cationic; Chemistry; Chemistry, Multidisciplinary; Communications; Copper; Fluorides; Fluorination; fluorine; Formations; homogeneous catalysis; Physical Sciences; Science & Technology; HALIDES; alkynes; carbene ligands; SUBSTITUTION-REACTIONS; MEDICINAL CHEMISTRY; ALCOHOLS; CYCLOADDITION; AMINATION; ALLYLIC FLUORIDES; BETA-KETOESTERS; homogeneous catalysis; ESTERS; copper; ALLENYLIDENE; fluorine

A catalytic method for the nucleophilic fluorination of propargylic electrophiles is described. Our protocol involves the use of a Cu(NHC) complex as the catalyst and is suitable for the preparation of secondary and tertiary propargylic fluorides without the formation of isomeric fluoroallenes. Prel...