Synthesis of Diaryl Selenium Compounds without Transition-Metal Catalyst

doi:10.6023/cjoc202303011

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (12): 4251-4260.DOI: 10.6023/cjoc202303011 Previous Articles Next Articles

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无过渡金属条件下二芳基硒化合物的合成

孙婧, 张萌萌, 锅小龙, 王琪, 王陆瑶^*()

首都师范大学化学系北京 100048

收稿日期:2023-03-06 修回日期:2023-05-29 发布日期:2023-07-27
基金资助:
国家自然科学基金(22074095); “十三五”期间北京市属高校高水平教师(CIT&TCD20190330)

Synthesis of Diaryl Selenium Compounds without Transition-Metal Catalyst

Jing Sun, Mengmeng Zhang, Xiaolong Guo, Qi Wang, Luyao Wang^*()

Department of Chemistry, Capital Normal University, Beijing 100048

Received:2023-03-06 Revised:2023-05-29 Published:2023-07-27
Contact: *E-mail: xdwly@163.com
Supported by:
National Natural Science Foundation of China(22074095); High-Level Teachers in Beijing Municipal Universities in the Period of 13th Five Year Plan(CIT&TCD20190330)

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Abstract

A series of diaryl selenium compounds were synthetized from N-arylamide compounds and diphenyl diselenide, using K₂S₂O₈ as oxidant without any transition metal catalyst. Mechanistic studies reveal that the reaction proceeds a single-electron transfer radical process. The dominant products are o-substituted and p-substituted product, depending on the stability of intermediates. The synthetic reaction exhibits some outstanding advantages, such as substrate tolerance, high regioselectivity, convenience and low-price.

Key words: transition metal-free, construction of C—Se bond, regional selectivity

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Jing Sun, Mengmeng Zhang, Xiaolong Guo, Qi Wang, Luyao Wang. Synthesis of Diaryl Selenium Compounds without Transition-Metal Catalyst[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4251-4260.

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Fig. & Tab. 11

Figure 1. Representative selenium-containing bioactive molecules

Scheme 1. Method of constructing C(sp2)—Se bond

Entry	Catalyst	Solvent	Oxidant	T/℃	Additive	Yield^b/%
1	Cu(OAc)₂	MeCN	K₂S₂O₈	100		56
2	FeCl₃	MeCN	K₂S₂O₈	100		79
3	Co(OAc)₂	MeCN	K₂S₂O₈	100		53
4		MeCN	K₂S₂O₈	100		78
5		MeCN	Ag₂CO₃	100		0
6		MeCN	PhI(OAc)₂	100		Trace
7		MeCN	Oxone	100		42
8		DCE	K₂S₂O₈	100		63
9		丙酮	K₂S₂O₈	100		0
10		DMSO	K₂S₂O₈	100		0
11		DMF	K₂S₂O₈	100		0
12		MeCN	K₂S₂O₈	80		Trace
13		MeCN	K₂S₂O₈	110		77
14		MeCN	K₂S₂O₈	100	KF	74
15		MeCN	K₂S₂O₈	100	Selectfluor	86
16^c		MeCN	K₂S₂O₈	100	Selectfluor	85

Table 1. Selection of optimum conditions for the construction of C—Se bond of arylamides

Table 2. Results of the reaction of various pyridine amides with diphenyl diselenethers

Table 3. Results of the reaction of various benzoyl amine with diphenyl diselenethers

Table 4. Reaction of various (cyclic) alkyl amides with diphenyl diselenethers

Scheme 2. Gram grade reaction

Scheme 3. Design experiment of free radical inhibitor additive

Scheme 4. Validation experiment of amide group necessity

Scheme 5. Necessity experiment of active H on N

Scheme 6. Inferred reaction mechanism of constructing C (sp2)—Se bond without transition metal is

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无过渡金属条件下二芳基硒化合物的合成

Synthesis of Diaryl Selenium Compounds without Transition-Metal Catalyst

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Fig. & Tab. 11

References 18

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