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Gold-Catalyzed Intramolecular Aminoarylation of Alkenes: C-C Bond Formation through Bimolecular Reductive Elimination

Brenzovich, William E., Jr. and Benitez, Diego and Lackner, Aaron D. and Shunatona, Hunter P. and Tkatchouk, Ekaterina and Goddard, William A., III and Toste, F. Dean (2010) Gold-Catalyzed Intramolecular Aminoarylation of Alkenes: C-C Bond Formation through Bimolecular Reductive Elimination. Angewandte Chemie International Edition, 49 (32). pp. 5519-5522. ISSN 1433-7851. PMCID PMC3433283.

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Gold-ilocks and the 3 mol % catalyst: Bimetallic gold bromides allow the room temperature aminoarylation of unactivated terminal olefins with aryl boronic acids using Selectfluor as an oxidant. A catalytic cycle involving gold(I)/gold(III) and a bimolecular reductive elimination for the key CC bond-forming step is proposed. dppm= bis(diphenylphosphanyl)methane.

Item Type:Article
Related URLs:
URLURL TypeDescription DOIArticle CentralArticle
Goddard, William A., III0000-0003-0097-5716
Toste, F. Dean0000-0001-8018-2198
Additional Information:© 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: May 6, 2010. Published online: July 2, 2010. F.D.T. gratefully acknowledges NIHGMS (R01 GM073932-04S1), Novartis, and Amgen for funding and Johnson Matthey for a generous donation of AuCl3. The MSC computational facilities were funded by grants from ARO-DURIP and ONR-DURIP.
Funding AgencyGrant Number
NIHR01 GM073932-04S1
Army Research Office (ARO)UNSPECIFIED
Office of Naval Research (ONR)UNSPECIFIED
Subject Keywords:alkenes; C-C bond formation; cyclization; gold; homogeneous catalysis
Issue or Number:32
PubMed Central ID:PMC3433283
Record Number:CaltechAUTHORS:20100830-142224179
Persistent URL:
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:19719
Deposited By: Tony Diaz
Deposited On:15 Sep 2010 19:41
Last Modified:28 Oct 2019 18:19

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