Base-catalyzed stereoselective thiosulfonylation of ynones for the facile synthesis of thio-functionalized vinyl sulfones

被引：15
作者：
Luo, Jinyun [1 ]
Lin, Muze [1 ]
Xia, Dengpeng [1 ]
Du, Guangfen [1 ]
Cai, Zhihua [1 ]
Dai, Bin [1 ]
He, Lin [1 ]
机构：
[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi 832000, Xinjiang Uygur, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 05期
基金：
中国国家自然科学基金;
关键词：
TRANSFER RADICAL-ADDITION; PHOTOREDOX CATALYSIS; TERMINAL ALKYNES; SULFUR; ACCESS; AMINOSULFONYLATION; ROUTE; LIGHT; CARBOSULFONYLATION; HALOSULFONYLATION;
D O I：
10.1039/d2qo01855a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first catalytic vicinal thiosulfonylation of ynones has been developed. Under the catalysis of 1-20 mol% Cs2CO3, various ynones underwent the Michael addition/nucleophilic substitution tandem reaction with different thiosulfonates to form C-SO2 and C-S bonds simultaneously and produced thio-functionalized vinyl sulfones in high yields and with excellent E-selectivity. In addition, on using K3PO4 as the base, ynones can couple with trifluoromethyl thiosulfonates through a similar tandem process to afford the corresponding trifluoromethylthiolated products in good to high yields with excellent stereoselectivity.
引用
收藏
页码：1224 / 1229
页数：6
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