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Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group

The use of cobalt as catalyst in direct C-H activation protocols as a replacement for more expensive second row transition metals is currently attracting significant attention. Herein we disclose a facile cobalt-catalyzed C-H functionalization route towards sultam motifs through annulation of easily prepared aryl sulfonamides and alkynes using 8-aminoquinoline as a directing group. The reaction shows broad substrate scope with products obtained in a highly regioselective manner in good to excellent isolated yields. Mechanistic insights suggest the formation of a Co(III)-aryl key species via a rate-determining arene C-H activation during the annulation reaction

We acknowledge financial support from the ERC for the Starting Grant Project ERC-2011-StG-277801 to X.R. and MINECO of Spain for CTQ2013-43012-P to X.R. and A.C, and a RyC contract to A.C.

Wiley

Manager: Ministerio de Economía y Competitividad (Espanya)
Author: Planas Fàbrega, Oriol
Whiteoak, Christopher J.
Company Casadevall, Anna
Ribas Salamaña, Xavi
Abstract: The use of cobalt as catalyst in direct C-H activation protocols as a replacement for more expensive second row transition metals is currently attracting significant attention. Herein we disclose a facile cobalt-catalyzed C-H functionalization route towards sultam motifs through annulation of easily prepared aryl sulfonamides and alkynes using 8-aminoquinoline as a directing group. The reaction shows broad substrate scope with products obtained in a highly regioselective manner in good to excellent isolated yields. Mechanistic insights suggest the formation of a Co(III)-aryl key species via a rate-determining arene C-H activation during the annulation reaction
We acknowledge financial support from the ERC for the Starting Grant Project ERC-2011-StG-277801 to X.R. and MINECO of Spain for CTQ2013-43012-P to X.R. and A.C, and a RyC contract to A.C.
Format: application/pdf
Document access: http://hdl.handle.net/10256/12495
Language: eng
Publisher: Wiley
Collection: info:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201500690
info:eu-repo/semantics/altIdentifier/issn/1615-4150
info:eu-repo/semantics/altIdentifier/eissn/1615-4169
info:eu-repo/grantAgreement/MINECO//CTQ2013-43012-P/ES/INVESTIGACIONES MECANISTICAS PARA SINTESIS ORGANICA SOSTENIBLE VIA ACTIVACION DE PEQUEÑAS MOLECULAS GASEOSAS Y DE ENLACES C-H CON METALES DE LA PRIMERA SERIE DE TRANSICION/
info:eu-repo/grantAgreement/EC/FP7/277801/EU/Sustainable C-X and C-H Functionalization Catalyzed by Copper(III) Species/SUSCATCU3
Rights: Tots els drets reservats
Subject: Alquins
Alkynes
Activació (Química)
Activation (Chemistry)
Reaccions químiques regioselectives
Chemical reactions
Sulfonamides
Sulfonamides
Title: Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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