Photo-triggered self-catalyzed fluoroalkylation/cyclization of unactivated alkenes: synthesis of quinazolinones containing the CFR group

A novel photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed. This transformation exhibits excellent substrate generality with respect to both the coupling partners. Of note is that this is t...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 23; no. 1; pp. 575 - 581
Main Authors Yang, Jin, Sun, Bin, Ding, Hao, Huang, Pan-Yi, Tang, Xiao-Li, Shi, Rong-Cheng, Yan, Zhi-Yang, Yu, Chuan-Ming, Jin, Can
Format Journal Article
Published 18.01.2021
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Abstract A novel photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed. This transformation exhibits excellent substrate generality with respect to both the coupling partners. Of note is that this is the first example describing the C sp 3 -Br bond homolysis of alkyl bromides via a substrate (quinazolinones) induced energy transfer process. Additionally, the mild conditions, tolerance to a wide range of functional groups and operational simplicity make this protocol practical for the synthesis of fluorine-containing ring-fused quinazolinones. A photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed.
AbstractList A novel photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed. This transformation exhibits excellent substrate generality with respect to both the coupling partners. Of note is that this is the first example describing the C sp 3 -Br bond homolysis of alkyl bromides via a substrate (quinazolinones) induced energy transfer process. Additionally, the mild conditions, tolerance to a wide range of functional groups and operational simplicity make this protocol practical for the synthesis of fluorine-containing ring-fused quinazolinones. A photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed.
Author Huang, Pan-Yi
Shi, Rong-Cheng
Ding, Hao
Yang, Jin
Tang, Xiao-Li
Jin, Can
Sun, Bin
Yan, Zhi-Yang
Yu, Chuan-Ming
AuthorAffiliation Zhejiang University of Technology
College of Pharmaceutical Sciences
Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals
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Title Photo-triggered self-catalyzed fluoroalkylation/cyclization of unactivated alkenes: synthesis of quinazolinones containing the CFR group
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