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Iron and Manganese Catalysts for the Selective Functionalization of Arene C(sp2)-H Bonds by Carbene Insertion

El mateix article està publicat en alemany a l’edició alemanya d’ ’Angewandte Chemie’ (ISSN 0044-8249, EISSN 1521-3757), 2016, vol. 128, núm. 22, p.6640–6644. DOI http://dx.doi.org/10.1002/ange.201601750

The first examples of the direct functionalization of non-activated aryl sp2 C-H bonds with ethyl diazoacetate (N2CHCO2Et) 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 FeII or MnII complexes bearing the tetradentate pytacn ligand (pytacn= 1-(2-pyridylmethyl)-4,7-dimethyl-1,4,7-triazacyclononane). When using alkylbenzenes, the alkylic C(sp3)-H bonds of the substituents remained unmodified, thus the reaction being also selective toward functionalization of sp2 C-H bonds. Exclusive catalysis: Iron- and-manganese-based catalysts selectively functionalize the C(sp2)-H bonds of benzene or alkylbenzenes through the formal insertion of the CHCO2Et group from N2CHCO2Et (see scheme). When using alkylbenzenes, the alkylic C(sp3)-H bonds of the substituents remain unmodified

Support for this work was provided by the MINECO (CTQ2014-52769-C3-R-1, CTQ2014-62234-EXP, CTQ2015-70795-P, CTQ2014-54306-P, and CTQ2014-52525P), and the Junta de Andaluc a (P10-FQM-06292)

© Angewandte Chemie International Edition, 2016, vol. 55, núm. 22, p. 6530-6534

Wiley

Manager: Ministerio de Economía y Competitividad (Espanya)
Author: Conde Fernández, Ana
Sabeña Vila, Gerard
Rodríguez Serrat, Mònica
Postils, Verònica
Luis Luis, Josep Maria
Díaz Requejo, M. Mar
Costas Salgueiro, Miquel
Pérez, Pedro J.
Abstract: El mateix article està publicat en alemany a l’edició alemanya d’ ’Angewandte Chemie’ (ISSN 0044-8249, EISSN 1521-3757), 2016, vol. 128, núm. 22, p.6640–6644. DOI http://dx.doi.org/10.1002/ange.201601750
The first examples of the direct functionalization of non-activated aryl sp2 C-H bonds with ethyl diazoacetate (N2CHCO2Et) 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 FeII or MnII complexes bearing the tetradentate pytacn ligand (pytacn= 1-(2-pyridylmethyl)-4,7-dimethyl-1,4,7-triazacyclononane). When using alkylbenzenes, the alkylic C(sp3)-H bonds of the substituents remained unmodified, thus the reaction being also selective toward functionalization of sp2 C-H bonds. Exclusive catalysis: Iron- and-manganese-based catalysts selectively functionalize the C(sp2)-H bonds of benzene or alkylbenzenes through the formal insertion of the CHCO2Et group from N2CHCO2Et (see scheme). When using alkylbenzenes, the alkylic C(sp3)-H bonds of the substituents remain unmodified
Support for this work was provided by the MINECO (CTQ2014-52769-C3-R-1, CTQ2014-62234-EXP, CTQ2015-70795-P, CTQ2014-54306-P, and CTQ2014-52525P), and the Junta de Andaluc a (P10-FQM-06292)
Format: application/pdf
ISSN: 1433-7851 (versió paper)
1521-3773 (versió electrònica)
Document access: http://hdl.handle.net/10256/13145
Language: eng
Publisher: Wiley
Collection: MINECO/PE 2015-2017/CTQ2014-54306-P
MINECO/PN 2011-2015/CTQ2014-52525-P
MINECO/PE 2016-2018/CTQ2015-70795-P
Reproducció digital del document publicat a: http://dx.doi.org/10.1002/anie.201601750
Articles publicats (D-Q)
info:eu-repo/grantAgreement/EC/FP7/239910
Is part of: © Angewandte Chemie International Edition, 2016, vol. 55, núm. 22, p. 6530-6534
Rights: Tots els drets reservats
Subject: Catalitzadors
Catalysts
Title: Iron and Manganese Catalysts for the Selective Functionalization of Arene C(sp2)-H Bonds by Carbene Insertion
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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