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- Publisher Website: 10.1002/anie.201911138
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- PMID: 31755156
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Article: Iridium(III)‐Catalyzed Intermolecular C(sp3)−H Insertion Reaction of Quinoid Carbene: A Radical Mechanism
Title | Iridium(III)‐Catalyzed Intermolecular C(sp3)−H Insertion Reaction of Quinoid Carbene: A Radical Mechanism |
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Authors | |
Keywords | carbenes diazo compounds homogeneous catalysis iridium radical reactions |
Issue Date | 2020 |
Publisher | Wiley - 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? |
Abstract | Described 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 Identifier | http://hdl.handle.net/10722/283041 |
ISSN | 2023 Impact Factor: 16.1 2023 SCImago Journal Rankings: 5.300 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Wang, HX | - |
dc.contributor.author | Richard, Y | - |
dc.contributor.author | Wan, Q | - |
dc.contributor.author | Zhou, CY | - |
dc.contributor.author | Che, CM | - |
dc.date.accessioned | 2020-06-05T06:24:18Z | - |
dc.date.available | 2020-06-05T06:24:18Z | - |
dc.date.issued | 2020 | - |
dc.identifier.citation | Angewandte Chemie (International Edition), 2020, v. 59 n. 5, p. 1845-1850 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.uri | http://hdl.handle.net/10722/283041 | - |
dc.description.abstract | Described 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.language | eng | - |
dc.publisher | Wiley - VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www3.interscience.wiley.com/journal/26737/home | - |
dc.relation.ispartof | Angewandte Chemie (International Edition) | - |
dc.rights | This 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.subject | carbenes | - |
dc.subject | diazo compounds | - |
dc.subject | homogeneous catalysis | - |
dc.subject | iridium | - |
dc.subject | radical reactions | - |
dc.title | Iridium(III)‐Catalyzed Intermolecular C(sp3)−H Insertion Reaction of Quinoid Carbene: A Radical Mechanism | - |
dc.type | Article | - |
dc.identifier.email | Wang, HX: wanghx1@hku.hk | - |
dc.identifier.email | Wan, Q: wendyqyw@hku.hk | - |
dc.identifier.email | Zhou, CY: cyzhou@hku.hk | - |
dc.identifier.email | Che, CM: chemhead@hku.hk | - |
dc.identifier.authority | Zhou, CY=rp00843 | - |
dc.identifier.authority | Che, CM=rp00670 | - |
dc.description.nature | postprint | - |
dc.identifier.doi | 10.1002/anie.201911138 | - |
dc.identifier.pmid | 31755156 | - |
dc.identifier.scopus | eid_2-s2.0-85076783331 | - |
dc.identifier.hkuros | 310313 | - |
dc.identifier.volume | 59 | - |
dc.identifier.issue | 5 | - |
dc.identifier.spage | 1845 | - |
dc.identifier.epage | 1850 | - |
dc.identifier.isi | WOS:000503055000001 | - |
dc.publisher.place | Germany | - |
dc.identifier.issnl | 1433-7851 | - |