C(sp3)–H fluorosulfonylvinylation/aza-Michael addition approach to FSO2-functionalized tetrahydropyridines

A novel cascade approach is presented for the synthesis of FSO2-functionalized tetrahydropyridines from propargyl alcohols, FSO2Cl, and anilines. This strategy successively involves radical fluorosulfonylation of the alkyne, C(sp3)–H fluorosulfonylvinylation, enamine formation, and intramolecular az...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2023-07, Vol.10 (15), p.3805-3810
Main Authors: Shi, Shuai, Zhao, Xueyan, Chen, Dengfeng, Luo, Jinyue, Liao, Saihu, Huang, Shenlin
Format: Article
Language:English
Subjects:
Alcohols
Alkynes
Aniline
Catalysts
Irradiation
Light irradiation
Organic chemistry
Propargyl alcohol
Radiation
Tetrahydropyridines
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Summary:A novel cascade approach is presented for the synthesis of FSO2-functionalized tetrahydropyridines from propargyl alcohols, FSO2Cl, and anilines. This strategy successively involves radical fluorosulfonylation of the alkyne, C(sp3)–H fluorosulfonylvinylation, enamine formation, and intramolecular aza-Michael addition. Notably, the fluorosulfonyl radical can be generated efficiently via simple blue light irradiation of an electron donor–acceptor (EDA) complex between propargyl alcohols and FSO2Cl, which requires no base, catalyst, and additive. The versatile follow-up derivatizations allow rapid ligation of tetrahydropyridines with other bioactive molecules that will be of value for drug discovery.
ISSN:2052-4110
2052-4110
DOI:10.1039/d3qo00639e