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Development of a palladium-catalyzed decarboxylative cross-coupling of (2-azaaryl)carboxylates with aryl halides

Haley, Christopher K. and Gilmore, Christopher D. and Stoltz, Brian M. (2013) Development of a palladium-catalyzed decarboxylative cross-coupling of (2-azaaryl)carboxylates with aryl halides. Tetrahedron, 69 (27-28). pp. 5732-5736. ISSN 0040-4020. PMCID PMC3686134. doi:10.1016/j.tet.2013.03.085.

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A catalytic method for the decarboxylative coupling of 2-(azaaryl)carboxylates with aryl halides is described. The decarboxylative cross-coupling presented is mediated by a system catalytic in both palladium and copper without requiring stoichiometric amounts of organometallic reagents or organoboronic acids. This method circumvents additional synthetic steps required to prepare 2-azaaryl organometallics and organoborates as nucleophilic coupling partners, which are prone to protodemetallation and protodeborylation and produce potentially toxic byproducts.

Item Type:Article
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URLURL TypeDescription CentralArticle
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2013 Elsevier Ltd. Received 6 February 2013. Received in revised form 15 March 2013. Accepted 19 March 2013. Available online 27 March 2013. Dedicated to Professor Melanie Sanford on receipt of the Tetrahedron Young Investigator Award. The authors wish to thank NIH-NIGMS (R01 GM080269) for financial support.
Funding AgencyGrant Number
NIHR01 GM080269
Subject Keywords:Decarboxylative cross-coupling; (2-Azaaryl)carboxylates; Palladium; Copper
Issue or Number:27-28
PubMed Central ID:PMC3686134
Record Number:CaltechAUTHORS:20130802-141019170
Persistent URL:
Official Citation:Christopher K. Haley, Christopher D. Gilmore, Brian M. Stoltz, Development of a palladium-catalyzed decarboxylative cross-coupling of (2-azaaryl)carboxylates with aryl halides, Tetrahedron, Volume 69, Issues 27–28, 8 July 2013, Pages 5732-5736, ISSN 0040-4020, (
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:39741
Deposited By: Ruth Sustaita
Deposited On:02 Aug 2013 21:29
Last Modified:09 Nov 2021 23:46

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