PhI(OAc)2-Promoted Dehydrogenation Oxidation for the Synthesis of 2-(Aryl/alkylthio)phenols and 10H-Phenothiazines

doi:10.6023/cjoc202201039

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (7): 2079-2088.DOI: 10.6023/cjoc202201039 Previous Articles Next Articles

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醋酸碘苯促进的脱氢氧化反应合成2-硫芳(烷)基苯酚及10H-吩噻嗪

曹廷舒, 魏向阳, 罗敏, 汪逸飞, 潘子俊, 徐程^*(), 殷国栋^*()

湖北师范大学化学化工学院污染物分析与资源化湖北省重点实验室湖北黄石 435002

收稿日期:2022-01-24 修回日期:2022-04-12 发布日期:2022-08-09
通讯作者: 徐程, 殷国栋
基金资助:
湖北省教育厅科学技术研究(D20192503)

PhI(OAc)₂-Promoted Dehydrogenation Oxidation for the Synthesis of 2-(Aryl/alkylthio)phenols and 10H-Phenothiazines

Tingshu Cao, Xiangyang Wei, Min Luo, Yifei Wang, Zijun Pan, Cheng Xu(), Guodong Yin()

Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, Hubei 435002

Received:2022-01-24 Revised:2022-04-12 Published:2022-08-09
Contact: Cheng Xu, Guodong Yin
Supported by:
Science and Technology Research Project of Educational Commission of Hubei Province(D20192503)

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Abstract

A PhI(OAc)₂-promoted reaction for the synthesis of 2-(aryl/alkylthio)phenol derivatives has been developed, which was realized via dehydrogenation oxidation between ortho-C(sp²)—H of phenols and S—H of thiophenols for direct formation of C—S bonds. Particularly, this method was also successfully applied for the efficient construction of tricyclic 10H-phenothiazines using 2-aminothiophenols as the substrates. All the newly synthesized products were identified by means of ¹H NMR, ¹³C NMR, IR and HRMS. Besides, 2-((4-bromophenyl)thio)benzene-1,4-diol (3i) was further confirmed by X-ray single crystal diffraction analysis. The method has the advantages of simple and easily available starting materials, mild reaction conditions, simple operation, as well as high atom economy.

Key words: 2-(aryl/alkylthio)phenols, 10H-phenothiazines, dehydrogenation oxidation, C—S bond formation

Cite this article

Tingshu Cao, Xiangyang Wei, Min Luo, Yifei Wang, Zijun Pan, Cheng Xu, Guodong Yin. PhI(OAc)₂-Promoted Dehydrogenation Oxidation for the Synthesis of 2-(Aryl/alkylthio)phenols and 10H-Phenothiazines[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2079-2088.

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Entry	Additive (equiv.)	Solvent	Temp./℃	Yield/%
1	None	MeCN/H₂O (V∶V=1∶1)	r.t.	70
2	HCOOH (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	64
3	HCl (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	68
4	CF₃COOH (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	92
5	FeCl₃ (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	86
6	ZnCl₂ (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	67
7	ZrCl₄ (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	75
8	AgOTf (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	83
9	Cu(OTf)₂ (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	80
10	I₂ (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	42
11	CF₃COOH (0.3)	MeCN/H₂O (V∶V=1∶1)	r.t.	89
12	CF₃COOH (0.1)	MeCN/H₂O (V∶V=1∶1)	r.t.	76
13	CF₃COOH (0.2)	MeCN/H₂O (V∶V=1∶2)	r.t.	64
14	CF₃COOH (0.2)	MeCN/H₂O (V∶V=2∶1)	r.t.	62
15	CF₃COOH (0.2)	MeCN/H₂O (V∶V=5∶1)	r.t.	51
16	CF₃COOH (0.2)	MeCN/H₂O (V∶V=1∶1)	40	82
17	CF₃COOH (0.2)	MeCN/H₂O (V∶V=1∶1)	60	65

Entry	Additive (equiv.)	Solvent	Temp./℃	Yield/%
1	None	MeCN/H₂O (V∶V=1∶1)	r.t.	70
2	HCOOH (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	64
3	HCl (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	68
4	CF₃COOH (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	92
5	FeCl₃ (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	86
6	ZnCl₂ (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	67
7	ZrCl₄ (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	75
8	AgOTf (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	83
9	Cu(OTf)₂ (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	80
10	I₂ (0.2)	MeCN/H₂O (V∶V=1∶1)	r.t.	42
11	CF₃COOH (0.3)	MeCN/H₂O (V∶V=1∶1)	r.t.	89
12	CF₃COOH (0.1)	MeCN/H₂O (V∶V=1∶1)	r.t.	76
13	CF₃COOH (0.2)	MeCN/H₂O (V∶V=1∶2)	r.t.	64
14	CF₃COOH (0.2)	MeCN/H₂O (V∶V=2∶1)	r.t.	62
15	CF₃COOH (0.2)	MeCN/H₂O (V∶V=5∶1)	r.t.	51
16	CF₃COOH (0.2)	MeCN/H₂O (V∶V=1∶1)	40	82
17	CF₃COOH (0.2)	MeCN/H₂O (V∶V=1∶1)	60	65

醋酸碘苯促进的脱氢氧化反应合成2-硫芳(烷)基苯酚及10H-吩噻嗪

PhI(OAc)₂-Promoted Dehydrogenation Oxidation for the Synthesis of 2-(Aryl/alkylthio)phenols and 10H-Phenothiazines

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