Photoredox Polychloroalkylation/Spirocyclization of Activated Alkynes via C(sp3)-H bond Cleavage

被引：1
|
作者：
Luo, Zhen-Tao [1 ]
Zhong, Long-Jin [1 ]
Zhou, Quan [1 ]
Xiong, Bi-Quan [1 ]
Tang, Ke-Wen [1 ]
Liu, Yu [1 ]
机构：
[1] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 06期
基金：
中国国家自然科学基金;
关键词：
photoredox; radical; polychloroalkylation; spiro[4,5]trienones; C(sp(3))-H bond cleavage; OXIDATIVE IPSO-ANNULATION; ALKENES; ACCESS; N-(P-METHOXYARYL)PROPIOLAMIDES; POLYHALOALKANES; SINTOKAMIDES; CYCLIZATION; METABOLITE; CHLORIDES; BARBAMIDE;
D O I：
10.1002/ejoc.202301159
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel strategy of visible-light photoredox catalysis ipso-annulation of activated alkynes with polychloroalkanes for the synthesis of 3-polychloroalkyl spiro[4,5]trienones, which used 4-methoxybenzenediazonium tetrafluoroborate salt as a hydrogen atom transfer reagent, is described. This polychloroalkylation/ spirocyclization of alkynes offers a widely range of 3-polychloroalkyl-spiro[4,5]trienone derivatives in high yields with a broad substrate scope via selective C(sp(3))-H homolytic cleavage. The results of controlled experiments showed that this method involves a radical process. The polyhaloalkyl radical species generated from intermolecular hydrogen atom transfer (HAT) between aryl radical and polychloroalkanes.
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页数：6
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