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Kinetic Resolution of Epoxides with CO 2 Catalyzed by a Chiral‐at‐Iridium Complex
Author(s) -
Qin Jie,
Larionov Vladimir A.,
Harms Klaus,
Meggers Eric
Publication year - 2019
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201802049
Subject(s) - epoxide , iridium , kinetic resolution , chemistry , catalysis , nucleophile , styrene , selectivity , polymer chemistry , polymerization , bromide , organic chemistry , enantioselective synthesis , copolymer , polymer
Chiral‐at‐metal bis‐cyclometalated iridium(III) complexes are introduced as a new class of chiral catalysts for the reaction of epoxides with CO 2 to form cyclic carbonates under conditions of kinetic resolution. Reactions are typically performed at room temperature in the presence of 1 mol % of iridium catalyst and 1.5 mol % of tetraethylammonium bromide as the nucleophilic cocatalyst to provide selectivity factors of up to 16.6. A variety of monosubstituted epoxides, including styrene epoxide, epoxides with aliphatic side chains, glycidyl ethers, and a glycidyl ester, are found to be suitable substrates. No polymerization side reaction is observed for any of the investigated substrates.