铜催化三组分反应合成含硫醚片段的三氮唑类化合物

doi:10.6023/cjoc202512045

摘要/Abstract

探索了一种基于环硫鎓盐亲核性开环反应构建含硫醚片段的三氮唑类化合物的新策略. 该方法利用环硫鎓盐可以被亲核试剂进攻开环的性质, 与叠氮基三甲基硅烷、炔烃发生多组分反应, 通过“一锅法”高效合成了一系列含有芳基/烷基硫醚片段的三氮唑类化合物. 该策略具有反应条件温和、后处理简单、产率优良、底物扩展性好等优点, 为含硫三氮唑类化合物的构建提供了一条便捷的新路径.

关键词: 铜催化, 三氮唑, Click反应, 硫鎓盐, 亲核性开环反应

A new strategy for the synthesis of triazoles compounds containing thioether fragments is established based on the nucleophilic ring-opening reaction of cyclic sulfonium salts. A variety of triazole compounds could be efficiently obtained through a multi- component reaction of cyclic sulfonium salts, TMSN₃, and alkynes. This strategy has the advantages of mild reaction conditions, operational simplicity, good to excellent yields, and good substrate tolerance, providing a convenient new strategy for the construction of sulfur-containing triazole compounds.

Key words: copper catalysis, triazoles, Click reaction, sulfonium salts, nucleophilic ring-opening reaction

引用此文

于丰恺, 朱先进, 徐紫涵, 石凌宇, 石永佳, 李旭锋, 杨道山. 铜催化三组分反应合成含硫醚片段的三氮唑类化合物[J]. 有机化学, 2026, 46(7): 2825-2834.

Fengkai Yu, Xianjin Zhu, Zihan Xu, Lingyu Shi, Yongjia Shi, Xufeng Li, Daoshan Yang. Copper-Catalyzed Three-Component Synthesis of Triazoles Containing Thioether Fragments[J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2825-2834.

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参考文献 19

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Entry	Catalyst	Base	Solvent	T/℃	Yield^b/%
1	CuI	Et₃N	THF	r.t.	25
2	CuI	Na₂CO₃	THF	r.t.	NR
3	CuI	t-BuONa	THF	r.t.	NR
4	CuI	DIPEA	THF	r.t.	15
5	CuI	Triphenylmine	THF	r.t.	NR
6	CuI	Pyrrolidine	THF	r.t.	10
7	CuI	DBU	THF	r.t.	NR
8^c	CuI	Et₃N	Other solvents instead of Et₃N	r.t.	0~20
9	CuI	Et₃N	Et₃N	r.t.	46
10	CuCl	Et₃N	Et₃N	r.t.	36
11	CuOAc	Et₃N	Et₃N	r.t.	37
12	Cu₂O	Et₃N	Et₃N	r.t.	25
13	CuSO₄	Et₃N	Et₃N	r.t.	NR
14	CuSO₄	NaAsc	MeOH	40	NR
15	CuI	Et₃N	Et₃N	0	NR
16	CuI	Et₃N	Et₃N	40	72
17	CuI	Et₃N	Et₃N	60	NR
18 ^d	CuI	Et₃N	Et₃N	40	66
19 ^e	CuI	Et₃N	Et₃N	40	57

Entry	Catalyst	Base	Solvent	T/℃	Yield^b/%
1	CuI	Et₃N	THF	r.t.	25
2	CuI	Na₂CO₃	THF	r.t.	NR
3	CuI	t-BuONa	THF	r.t.	NR
4	CuI	DIPEA	THF	r.t.	15
5	CuI	Triphenylmine	THF	r.t.	NR
6	CuI	Pyrrolidine	THF	r.t.	10
7	CuI	DBU	THF	r.t.	NR
8^c	CuI	Et₃N	Other solvents instead of Et₃N	r.t.	0~20
9	CuI	Et₃N	Et₃N	r.t.	46
10	CuCl	Et₃N	Et₃N	r.t.	36
11	CuOAc	Et₃N	Et₃N	r.t.	37
12	Cu₂O	Et₃N	Et₃N	r.t.	25
13	CuSO₄	Et₃N	Et₃N	r.t.	NR
14	CuSO₄	NaAsc	MeOH	40	NR
15	CuI	Et₃N	Et₃N	0	NR
16	CuI	Et₃N	Et₃N	40	72
17	CuI	Et₃N	Et₃N	60	NR
18 ^d	CuI	Et₃N	Et₃N	40	66
19 ^e	CuI	Et₃N	Et₃N	40	57