Electrochemical cascade migratory versus ortho-cyclization of 2-alkynylbenzenesulfonamides

Efficient control over several possible reaction pathways of free radicals is the chemical basis of their highly selective transformations. Among various competing reaction pathways, sulfonimidyl radicals generated from the electrolysis of 2-alkynylbenzenesulfonamides undergo cascade migratory or or...

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Published inChemical science (Cambridge) Vol. 15; no. 8; pp. 2827 - 2832
Main Authors Shi, Zhaojiang, Dong, Shicheng, Liu, Ting, Wang, Wei-Zhen, Li, Nan, Yuan, Yaofeng, Zhu, Jun, Ye, Ke-Yin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 22.02.2024
Royal Society of Chemistry
The Royal Society of Chemistry
Subjects
Cations
Chemistry
Chemistry, Multidisciplinary
Electrolysis
Free radicals
Physical Sciences
Science & Technology
OXIDATION
REAGENTS
C-H FUNCTIONALIZATION
RADICAL CASCADE
LIGHT
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Summary:Efficient control over several possible reaction pathways of free radicals is the chemical basis of their highly selective transformations. Among various competing reaction pathways, sulfonimidyl radicals generated from the electrolysis of 2-alkynylbenzenesulfonamides undergo cascade migratory or ortho-cyclization cyclization selectively. It is found that the incorporation of an extra 2-methyl substituent biases the selective migration of the acyl- over vinyl-linker of the key spirocyclic cation intermediate and thus serves as an enabling handle to achieve the synthetically interesting yet under-investigated cascade migratory cyclization of spirocyclic cations.
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These authors contributed equally to this work.
ISSN:2041-6520
2041-6539
DOI:10.1039/d3sc05229j