Visible‐Light‐Driven Base‐Promoted Radical Cascade Difluoroalkylation‐Cyclization‐Iodination of 1,6‐Enynes with Ethyl Difluoroiodoacetate

A visible‐light‐driven base‐promoted radical cascade difluoroalkylation/5‐exo‐dig cyclization/iodination of 1,6‐enynes with ethyl difluoroiodoacetate was developed under catalyst‐free and oxidant‐free conditions. The difluoroalkylated pyrrolidines and tetrahydrofuran derivatives were generated with...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-02, Vol.2022 (5), p.n/a
Main Authors: Wang, Yan, Liu, Ruyan, Zhou, Pengsheng, Wu, Jianglong, Li, Wenshuang, Wang, Chenyu, Li, Hao, Li, Dianjun, Yang, Jinhui
Format: Article
Language:English
Subjects:
Base-promoted
Cyclization
Difluoroalkylation
Functional groups
Iodination
Oxidizing agents
Radical reactions
Stereoselectivity
Tetrahydrofuran
Visible-light-driven
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Summary:A visible‐light‐driven base‐promoted radical cascade difluoroalkylation/5‐exo‐dig cyclization/iodination of 1,6‐enynes with ethyl difluoroiodoacetate was developed under catalyst‐free and oxidant‐free conditions. The difluoroalkylated pyrrolidines and tetrahydrofuran derivatives were generated with good functional group tolerance and high Z/E stereoselectivity. This reaction provided an alternative and mild method for the preparation of highly functionalized and vinyl C−I bonds containing five‐membered heterocyclic products. A visible‐light‐driven base‐enabled free radical reaction of 1,6‐enynes and ICF2COOEt was developed via cascade difluoroalkylation/5‐exo‐dig cyclization/iodination without catalyst and oxidants. The reaction provided difluoroalkylated and vinyl C−I bonds containing pyrrolidines and tetrahydrofuran derivatives in good yields and excellent Z/E stereoselectivity.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202101395