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Article: Iridium(III)‐Catalyzed Intermolecular C(sp3)−H Insertion Reaction of Quinoid Carbene: A Radical Mechanism

TitleIridium(III)‐Catalyzed Intermolecular C(sp3)−H Insertion Reaction of Quinoid Carbene: A Radical Mechanism
Authors
Keywordscarbenes
diazo compounds
homogeneous catalysis
iridium
radical reactions
Issue Date2020
PublisherWiley - VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www3.interscience.wiley.com/journal/26737/home
Citation
Angewandte Chemie (International Edition), 2020, v. 59 n. 5, p. 1845-1850 How to Cite?
AbstractDescribed herein is an IrIII/porphyrin‐catalyzed intermolecular C(sp3)−H insertion reaction of a quinoid carbene (QC). The reaction was designed by harnessing the hydrogen‐atom transfer (HAT) reactivity of a metal‐QC species with aliphatic substrates followed by a radical rebound process to afford C−H arylation products. This methodology is efficient for the arylation of activated hydrocarbons such as 1,4‐cyclohexadienes (down to 40 min reaction time, up to 99 % yield, up to 1.0 g scale). It features unique regioselectivity, which is mainly governed by steric effects, as the insertion into primary C−H bonds is favored over secondary and/or tertiary C−H bonds in the substituted cyclohexene substrates. Mechanistic studies revealed a radical mechanism for the reaction.
Persistent Identifierhttp://hdl.handle.net/10722/283041
ISSN
2023 Impact Factor: 16.1
2023 SCImago Journal Rankings: 5.300
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorWang, HX-
dc.contributor.authorRichard, Y-
dc.contributor.authorWan, Q-
dc.contributor.authorZhou, CY-
dc.contributor.authorChe, CM-
dc.date.accessioned2020-06-05T06:24:18Z-
dc.date.available2020-06-05T06:24:18Z-
dc.date.issued2020-
dc.identifier.citationAngewandte Chemie (International Edition), 2020, v. 59 n. 5, p. 1845-1850-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://hdl.handle.net/10722/283041-
dc.description.abstractDescribed herein is an IrIII/porphyrin‐catalyzed intermolecular C(sp3)−H insertion reaction of a quinoid carbene (QC). The reaction was designed by harnessing the hydrogen‐atom transfer (HAT) reactivity of a metal‐QC species with aliphatic substrates followed by a radical rebound process to afford C−H arylation products. This methodology is efficient for the arylation of activated hydrocarbons such as 1,4‐cyclohexadienes (down to 40 min reaction time, up to 99 % yield, up to 1.0 g scale). It features unique regioselectivity, which is mainly governed by steric effects, as the insertion into primary C−H bonds is favored over secondary and/or tertiary C−H bonds in the substituted cyclohexene substrates. Mechanistic studies revealed a radical mechanism for the reaction.-
dc.languageeng-
dc.publisherWiley - VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www3.interscience.wiley.com/journal/26737/home-
dc.relation.ispartofAngewandte Chemie (International Edition)-
dc.rightsThis is the peer reviewed version of the following article: Angewandte Chemie (International Edition), 2020, v. 59 n. 5, p. 1845-1850, which has been published in final form at https://doi.org/10.1002/anie.201911138. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.-
dc.subjectcarbenes-
dc.subjectdiazo compounds-
dc.subjecthomogeneous catalysis-
dc.subjectiridium-
dc.subjectradical reactions-
dc.titleIridium(III)‐Catalyzed Intermolecular C(sp3)−H Insertion Reaction of Quinoid Carbene: A Radical Mechanism-
dc.typeArticle-
dc.identifier.emailWang, HX: wanghx1@hku.hk-
dc.identifier.emailWan, Q: wendyqyw@hku.hk-
dc.identifier.emailZhou, CY: cyzhou@hku.hk-
dc.identifier.emailChe, CM: chemhead@hku.hk-
dc.identifier.authorityZhou, CY=rp00843-
dc.identifier.authorityChe, CM=rp00670-
dc.description.naturepostprint-
dc.identifier.doi10.1002/anie.201911138-
dc.identifier.pmid31755156-
dc.identifier.scopuseid_2-s2.0-85076783331-
dc.identifier.hkuros310313-
dc.identifier.volume59-
dc.identifier.issue5-
dc.identifier.spage1845-
dc.identifier.epage1850-
dc.identifier.isiWOS:000503055000001-
dc.publisher.placeGermany-
dc.identifier.issnl1433-7851-

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