Construction of highly congested quaternary carbon centers by NHC catalysis through dearomatization

A NHC-catalyzed hypervalent iodine reagents and transition-metal free redox-neutral dearomatization of phenols is reported. This protocol provides an efficient access for highly congested quaternatry carbon centers construction. It also features operationally simplicity, mild reaction conditions and...

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Main Authors: Lixia Liu, Cong-Ying Zhou, Chengming Wang
Format: Article
Language:English
Published: KeAi Communications Co. Ltd. 2023-08-01
Series:Green Synthesis and Catalysis
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S2666554922000618
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author Lixia Liu
Cong-Ying Zhou
Chengming Wang
author_facet Lixia Liu
Cong-Ying Zhou
Chengming Wang
author_sort Lixia Liu
collection DOAJ
description A NHC-catalyzed hypervalent iodine reagents and transition-metal free redox-neutral dearomatization of phenols is reported. This protocol provides an efficient access for highly congested quaternatry carbon centers construction. It also features operationally simplicity, mild reaction conditions and good functional group tolerance. Moreover, the reported procedure can be easily emplified to 1 ​g scale. Mechanism study reveals the dearomative transformation possibly undergoes a single electron transfer process with NHC radical cation as a reactive intermediate.
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spelling doaj.art-dd06b49cce4842deb9f0fefe666afd102023-08-23T04:34:23ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492023-08-0143263267Construction of highly congested quaternary carbon centers by NHC catalysis through dearomatizationLixia Liu0Cong-Ying Zhou1Chengming Wang2College of Chemistry and Materials Science, Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, Jinan University, Guangzhou 510632, ChinaCorresponding authors.; College of Chemistry and Materials Science, Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, Jinan University, Guangzhou 510632, ChinaCorresponding authors.; College of Chemistry and Materials Science, Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, Jinan University, Guangzhou 510632, ChinaA NHC-catalyzed hypervalent iodine reagents and transition-metal free redox-neutral dearomatization of phenols is reported. This protocol provides an efficient access for highly congested quaternatry carbon centers construction. It also features operationally simplicity, mild reaction conditions and good functional group tolerance. Moreover, the reported procedure can be easily emplified to 1 ​g scale. Mechanism study reveals the dearomative transformation possibly undergoes a single electron transfer process with NHC radical cation as a reactive intermediate.http://www.sciencedirect.com/science/article/pii/S2666554922000618NHCQuaternary carbon centerDearomatizationRadicalSET
spellingShingle Lixia Liu
Cong-Ying Zhou
Chengming Wang
Construction of highly congested quaternary carbon centers by NHC catalysis through dearomatization
Green Synthesis and Catalysis
NHC
Quaternary carbon center
Dearomatization
Radical
SET
title Construction of highly congested quaternary carbon centers by NHC catalysis through dearomatization
title_full Construction of highly congested quaternary carbon centers by NHC catalysis through dearomatization
title_fullStr Construction of highly congested quaternary carbon centers by NHC catalysis through dearomatization
title_full_unstemmed Construction of highly congested quaternary carbon centers by NHC catalysis through dearomatization
title_short Construction of highly congested quaternary carbon centers by NHC catalysis through dearomatization
title_sort construction of highly congested quaternary carbon centers by nhc catalysis through dearomatization
topic NHC
Quaternary carbon center
Dearomatization
Radical
SET
url http://www.sciencedirect.com/science/article/pii/S2666554922000618
work_keys_str_mv AT lixialiu constructionofhighlycongestedquaternarycarboncentersbynhccatalysisthroughdearomatization
AT congyingzhou constructionofhighlycongestedquaternarycarboncentersbynhccatalysisthroughdearomatization
AT chengmingwang constructionofhighlycongestedquaternarycarboncentersbynhccatalysisthroughdearomatization