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Iron and Manganese Catalysts for the Selective Functionalization of Arene C(sp 2 )−H Bonds by Carbene Insertion
Author(s) -
Conde Ana,
Sabenya Gerard,
Rodríguez Mònica,
Postils Verònica,
Luis Josep M.,
DíazRequejo M. Mar,
Costas Miquel,
Pérez Pedro J.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201601750
Subject(s) - carbene , chemistry , surface modification , catalysis , cycloheptatriene , manganese , medicinal chemistry , ligand (biochemistry) , ethyl diazoacetate , alkylbenzenes , aryl , stereochemistry , cyclopropanation , polymer chemistry , organic chemistry , biochemistry , receptor , alkyl
The first examples of the direct functionalization of non‐activated aryl sp 2 C−H bonds with ethyl diazoacetate (N 2 CHCO 2 Et) catalyzed by Mn‐ or Fe‐based complexes in a completely selective manner are reported, with no formation of the frequently observed cycloheptatriene derivatives through competing Buchner reaction. The best catalysts are Fe II or Mn II complexes bearing the tetradentate pytacn ligand (pytacn= 1‐(2‐pyridylmethyl)‐4,7‐dimethyl‐1,4,7‐triazacyclononane). When using alkylbenzenes, the alkylic C(sp 3 )−H bonds of the substituents remained unmodified, thus the reaction being also selective toward functionalization of sp 2 C−H bonds.