Copper-Catalyzed Decarboxylative Cross-Coupling of Carboxylic Acids and Arylcarbamoyl Chlorides

doi:10.6023/cjoc202007071

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1146-1152.DOI: 10.6023/cjoc202007071 Previous Articles Next Articles

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铜催化羧酸与芳氨基甲酰氯的脱羧交叉偶联

周敦¹, 樊爱红¹, 李翔¹, 陈春霞¹^,^*(), 孙鹏¹, 彭进松¹^,^*()

1 东北林业大学化学化工与资源利用学院哈尔滨 150040

收稿日期:2020-07-30 修回日期:2020-10-20 发布日期:2020-11-19
通讯作者: 陈春霞, 彭进松
基金资助:
中央高校基本科研业务费专项资金(2572019CG06); 中央高校基本科研业务费专项资金(2572020DR07); 黑龙江省自然科学基金(LC2018003); 黑龙江省自然科学基金(B2017002); 高等学校学科创新引智计划(111计划)(B20088)

Copper-Catalyzed Decarboxylative Cross-Coupling of Carboxylic Acids and Arylcarbamoyl Chlorides

Dun Zhou¹, Aihong Fan¹, Xiang Li¹, Chunxia Chen¹^,^*(), Peng Sun¹, Jinsong Peng¹^,^*()

1 College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, Harbin 150040

Received:2020-07-30 Revised:2020-10-20 Published:2020-11-19
Contact: Chunxia Chen, Jinsong Peng
About author:
* Corresponding authors. E-mail: ccx0109@nefu.edu.cn;
jspeng1998@nefu.edu.cn
Supported by:
Fundamental Research Funds for the Central Universities(2572019CG06); Fundamental Research Funds for the Central Universities(2572020DR07); Natural Science Foundation of Heilongjiang Province(LC2018003); Natural Science Foundation of Heilongjiang Province(B2017002); Programme of Introducing Talents of Discipline to Universities (111 Project）(B20088)

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Abstract

A ligand-free copper-catalyzed decarboxylative cross-coupling reaction of carboxylic acids and carbamoyl chlorides in the absence of base was developed. With CuCl₂ as the catalyst, the decarboxylative cross-coupling process could be realized in benzene at 120 ℃ in 48 h. Under the standard condition, the catalytic system had good functional group tolerance, and diverse amides were obtained in good to high yields. The structures of products were elucidated by ¹H NMR, ¹³C NMR and HRMS spectra.

Key words: copper-catalysis, decarboxylative cross-coupling, C—C bond formation, arylcarbamoyl chloride, amide

Cite this article

Dun Zhou, Aihong Fan, Xiang Li, Chunxia Chen, Peng Sun, Jinsong Peng. Copper-Catalyzed Decarboxylative Cross-Coupling of Carboxylic Acids and Arylcarbamoyl Chlorides[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1146-1152.

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铜催化羧酸与芳氨基甲酰氯的脱羧交叉偶联

Copper-Catalyzed Decarboxylative Cross-Coupling of Carboxylic Acids and Arylcarbamoyl Chlorides

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Entry	Cu	Solvent	Time/h	Yield^b/%
1^c	Cu(OAc)₂	Benzene	24	32
2^c	CuCl₂	Benzene	24	53
3^c	CuI/CuBr/CuCl	Benzene	24	0
4^c	CuO	Benzene	24	0
5^c	Cu(OTf)₂	Benzene	24	0
6^c^,^d	CuCl₂	Benzene	24	25
7^c^,^e	CuCl₂	Benzene	24	30
8	CuCl₂	o-Xylene	24	38
9	CuCl₂	m-Xylene	24	11
10	CuCl₂	THF	24	Trace
11	CuCl₂	Xylene	24	60
12	CuCl₂	Toluene	24/48	Trace
13	CuCl₂	Benzene	24	69
14	CuCl₂	CH₃CN	24	Trace
15	CuCl₂	DMF	24	0
16	CuCl₂	DMSO	24	Trace
17	CuCl₂	Benzene	36	79
18	CuCl₂	Benzene	48	81

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