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Orthogonal Selectivity in C–H Olefination: Synthesis of Branched Vinylarene with Unactivated Aliphatic Substitution
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Number of Authors: 82019 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 9, no 10, p. 9606-9613Article in journal (Refereed) Published
Abstract [en]

Oxidative coupling is a useful tool to synthesize vinylarenes. Despite remarkable successes in linear vinylarene, branched vinylarene synthesis has remained underdeveloped. Overcoming this limitation, herein, we report a chelation-assisted oxidative coupling to generate branched olefinated product in high yield. Exclusive branched selectivity was obtained using alkenyl carboxylic acid. Detailed experimental studies combined with computational investigations suggest that beta-migratory insertion, followed by a decarboxylation pathway is operative for the overall transformation.

Place, publisher, year, edition, pages
2019. Vol. 9, no 10, p. 9606-9613
Keywords [en]
branched olefin, palladium, orthogonal selectivity, drug diversification, decarboxylation
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-175852DOI: 10.1021/acscatal.9b03019ISI: 000489204000086OAI: oai:DiVA.org:su-175852DiVA, id: diva2:1369356
Available from: 2019-11-11 Created: 2019-11-11 Last updated: 2019-11-11Bibliographically approved

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Szabó, Kálmán J.Maiti, Debabrata
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