Quantum hydrogen tunneling promoting halogen-atom and group transfer chemistry

A quantum-hydrogen-tunneling-controlled halogen-atom and group transfer strategy has been successfully developed to generate carbon radicals by using the substituted cyclohexadiene as the abstractor under mild photochemical conditions, in which alkyl and aryl halides as well as numerous alcohol and...

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Main Authors: Xiao Xiao, Yi-Ping Yao, Biao Chen, Chuan Xiang Alvin Tan, Fen-Er Chen
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/S2666554922001284
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author Xiao Xiao
Yi-Ping Yao
Biao Chen
Chuan Xiang Alvin Tan
Fen-Er Chen
author_facet Xiao Xiao
Yi-Ping Yao
Biao Chen
Chuan Xiang Alvin Tan
Fen-Er Chen
author_sort Xiao Xiao
collection DOAJ
description A quantum-hydrogen-tunneling-controlled halogen-atom and group transfer strategy has been successfully developed to generate carbon radicals by using the substituted cyclohexadiene as the abstractor under mild photochemical conditions, in which alkyl and aryl halides as well as numerous alcohol and thiol analogues can be activated. Mechanism investigation unveiled that this process is inhibited from thermodynamic and kinetic effects but is rendered successful through quantum tunneling.
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spelling doaj.art-cf77c95fa6644c9b8ebe1cfc63d07dd52023-08-23T04:34:23ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492023-08-0143187189Quantum hydrogen tunneling promoting halogen-atom and group transfer chemistryXiao Xiao0Yi-Ping Yao1Biao Chen2Chuan Xiang Alvin Tan3Fen-Er Chen4Institute of Pharmaceutical Science and Technology, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, ChinaInstitute of Pharmaceutical Science and Technology, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, ChinaInstitute of Pharmaceutical Science and Technology, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, ChinaDepartment of Chemistry, National University of Singapore, 3 Science Drive 3 117543, SingaporeInstitute of Pharmaceutical Science and Technology, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China; Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University, Shanghai 200433, China; Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai 200433, China; Corresponding author. Institute of Pharmaceutical Science and Technology, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.A quantum-hydrogen-tunneling-controlled halogen-atom and group transfer strategy has been successfully developed to generate carbon radicals by using the substituted cyclohexadiene as the abstractor under mild photochemical conditions, in which alkyl and aryl halides as well as numerous alcohol and thiol analogues can be activated. Mechanism investigation unveiled that this process is inhibited from thermodynamic and kinetic effects but is rendered successful through quantum tunneling.http://www.sciencedirect.com/science/article/pii/S2666554922001284Quantum hydrogen tunnelingHalogen-atom and group transferCarbon radicalsSubstituted cyclohexadienePhotocatalysis
spellingShingle Xiao Xiao
Yi-Ping Yao
Biao Chen
Chuan Xiang Alvin Tan
Fen-Er Chen
Quantum hydrogen tunneling promoting halogen-atom and group transfer chemistry
Green Synthesis and Catalysis
Quantum hydrogen tunneling
Halogen-atom and group transfer
Carbon radicals
Substituted cyclohexadiene
Photocatalysis
title Quantum hydrogen tunneling promoting halogen-atom and group transfer chemistry
title_full Quantum hydrogen tunneling promoting halogen-atom and group transfer chemistry
title_fullStr Quantum hydrogen tunneling promoting halogen-atom and group transfer chemistry
title_full_unstemmed Quantum hydrogen tunneling promoting halogen-atom and group transfer chemistry
title_short Quantum hydrogen tunneling promoting halogen-atom and group transfer chemistry
title_sort quantum hydrogen tunneling promoting halogen atom and group transfer chemistry
topic Quantum hydrogen tunneling
Halogen-atom and group transfer
Carbon radicals
Substituted cyclohexadiene
Photocatalysis
url http://www.sciencedirect.com/science/article/pii/S2666554922001284
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AT yipingyao quantumhydrogentunnelingpromotinghalogenatomandgrouptransferchemistry
AT biaochen quantumhydrogentunnelingpromotinghalogenatomandgrouptransferchemistry
AT chuanxiangalvintan quantumhydrogentunnelingpromotinghalogenatomandgrouptransferchemistry
AT fenerchen quantumhydrogentunnelingpromotinghalogenatomandgrouptransferchemistry