Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 39, Pages 15509-15514Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b08632
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Funding
- ICIQ Starting Career Programme
- Agencia Estatal de Investigacion (AEI) of the Ministerio de Ciencia, Innovation y Universidades [CTQ2016-75311-P]
- CEL-LEX Foundation through the CELLEX-ICIQ high-throughput experimentation platform
- CERCA Programme (Generalitat de Catalunya)
- European Union [794815]
- AEI [BES-2017-080163]
- Marie Curie Actions (MSCA) [794815] Funding Source: Marie Curie Actions (MSCA)
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We report a catalytic strategy that generates rhodium-carbynoids by selective diazo activation of designed carbyne sources. We found that rhodium-carbynoid species provoke C(sp(2))-C(sp(2)) bond scission in alkenes by inserting a monovalent carbon unit between both sp(2)-hybridized carbons. This skeletal remodeling process accesses synthetically useful allyl cation intermediates that conduct to valuable allylic building blocks upon nucleophile attack. Our results rely on the formation of cyclopropyl-I (III) intermediates able to undergo electro-cyclic ring-opening, following the Woodward-Hoff-mann-DePuy rules.
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