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Access to Trisubstituted Fluoroalkenes by Ruthenium‐Catalyzed Cross‐Metathesis
Author(s) -
Nouaille Augustin,
Pannecoucke Xavier,
Poisson Thomas,
CouveBonnaire Samuel
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001612
Subject(s) - ruthenium , chemistry , olefin metathesis , salt metathesis reaction , metathesis , catalysis , olefin fiber , combinatorial chemistry , organic chemistry , polymerization , polymer
Although the olefin metathesis reaction is a well‐known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross‐Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post‐functionalizable source of fluoroalkene, that we found as the methyl 2‐fluoroacrylate. We reported herein the efficient ruthenium‐catalyzed CM reaction of various terminal and internal alkenes with methyl 2‐fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products.