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Formal C−H Carboxylation of Unactivated Arenes
Author(s) -
Gevorgyan Ashot,
Hopmann Kathrin H.,
Bayer Annette
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000515
Subject(s) - carboxylation , regioselectivity , steric effects , chemistry , catalysis , organic chemistry , combinatorial chemistry , medicinal chemistry , stereochemistry
A formal C−H carboxylation of unactivated arenes using CO 2 in green solvents is described. The present strategy combines a sterically controlled Ir‐catalyzed C−H borylation followed by a Cu‐catalyzed carboxylation of the in situ generated organoboronates. The reaction is highly regioselective for the C−H carboxylation of 1,3‐disubstituted and 1,2,3‐trisubstituted benzenes, 1,2‐ or 1,4‐symmetrically substituted benzenes, fluorinated benzenes and different heterocycles. The developed methodology was applied to the late‐stage C−H carboxylation of commercial drugs and ligands.