o-Iodoarylation of Thiols Enabled by Aryne Generated from o-Diiodoarene and Sodium Hydride

doi:10.6023/cjoc202312022

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (7): 2363-2370.DOI: 10.6023/cjoc202312022 Previous Articles Next Articles

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邻二碘芳烃和氢化钠产生芳炔用于硫醇的邻碘芳基化反应

刘典范, 王健智, 王梦晴, 陈晓蓓, 胡延维^*(), 张士磊^*()

苏州大学药学院江苏省重大神经精神疾病研究重点实验室江苏省精准诊疗药物创制工程研究中苏苏州 215123

收稿日期:2023-12-23 修回日期:2024-03-08 发布日期:2024-03-20
基金资助:
国家自然科学基金(22271206); 国家自然科学基金(22071053); 江苏省高校重点学科建设(PAPD); 苏州市脑病诊疗国际联合实验室资助项目

o-Iodoarylation of Thiols Enabled by Aryne Generated from o-Diiodoarene and Sodium Hydride

Dianfan Liu, Jianzhi Wang, Mengqing Wang, Xiaobei Chen, Yanwei Hu(), Shilei Zhang()

Jiangsu Key Laboratory of Neuropsychiatric Diseases, Jiangsu Province Engineering Research Center of Precision Diagnostics and Therapeutics Development, College of Pharmaceutical Sciences,Soochow University, Suzhou, Jiangsu 215123

Received:2023-12-23 Revised:2024-03-08 Published:2024-03-20
Contact: * E-mail: huyanwei@suda.edu.cn;zhangshilei@suda.edu.cn
Supported by:
National Natural Science Foundation of China(22271206); National Natural Science Foundation of China(22071053); Priority Academic Program Development of Jiangsu Higher Education Institutions(PAPD); Suzhou International Joint Laboratory for Diagnosis and Treatment of Brain Diseases.

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Abstract

A simple and efficient method is described for the synthesis of o-iodoaryl thioethers by the reaction of thiols and aryne. The aryne is generated from inexpensive and readily available reagents o-diiodoarene and sodium hydride. Remarkably, no disulfide substituted byproduct was observed in the reactions which is different from transition metal-catalyzed process. This method features simple operation, mild reaction conditions, broad substrate scope, and high reaction yields for many cases.

Key words: aryne, thiol, o-diiodoarene, sodium hydride, o-iodoaryl thioether

Cite this article

Dianfan Liu, Jianzhi Wang, Mengqing Wang, Xiaobei Chen, Yanwei Hu, Shilei Zhang. o-Iodoarylation of Thiols Enabled by Aryne Generated from o-Diiodoarene and Sodium Hydride[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2363-2370.

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Entry	Base (equiv.)	Solvent	T/℃	Yield^b/%
1	NaH (3.0)	THF	rt	52
2	NaH (3.0)	THF	35	56
3	NaH (3.0)	THF	40	71
4	NaH (3.0)	THF	50	65
5	NaH (3.0)	THF	60	42
6	NaH (5.0)	THF	40	68
7^c	NaH (3.0)	THF	40	56
8	NaH (3.0)	DMA	40	63
9	NaH (3.0)	CH₃CN	40	12
10	NaH (3.0)	Dioxane	40	nr^d
11	NaH (3.0)	DMF	40	36
12	KH (3.0)	THF	40	nr
13	CaH₂ (2.0)	THF	40	24
14	LiH (3.0)	THF	40	nr
15	BuLi (2.5)	THF	-78	35
16^e	NaH (3.0)	THF	40	36
17	K₂CO₃ (2.0)	DMA	40	nr
18	NaOH (3.0)	DMA	40	nr

Entry	Base (equiv.)	Solvent	T/℃	Yield^b/%
1	NaH (3.0)	THF	rt	52
2	NaH (3.0)	THF	35	56
3	NaH (3.0)	THF	40	71
4	NaH (3.0)	THF	50	65
5	NaH (3.0)	THF	60	42
6	NaH (5.0)	THF	40	68
7^c	NaH (3.0)	THF	40	56
8	NaH (3.0)	DMA	40	63
9	NaH (3.0)	CH₃CN	40	12
10	NaH (3.0)	Dioxane	40	nr^d
11	NaH (3.0)	DMF	40	36
12	KH (3.0)	THF	40	nr
13	CaH₂ (2.0)	THF	40	24
14	LiH (3.0)	THF	40	nr
15	BuLi (2.5)	THF	-78	35
16^e	NaH (3.0)	THF	40	36
17	K₂CO₃ (2.0)	DMA	40	nr
18	NaOH (3.0)	DMA	40	nr

邻二碘芳烃和氢化钠产生芳炔用于硫醇的邻碘芳基化反应

o-Iodoarylation of Thiols Enabled by Aryne Generated from o-Diiodoarene and Sodium Hydride

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