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

ARTICLES

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)

1. cjoc202007071辅助材料.pdf(1977KB)

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

References 28

[1]	(a) Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606. pmid: 27673596
	(b) de Figueiredo, R.M.; Suppo,, J.-S.; Campagne,, J.-M. Chem. Rev. 2016, 116, 12029. pmid: 27673596
[2]	Roy, S.; Roy, S.; Gribble, G. W. Tetrahedron 2012, 68, 9867.
[3]	Organotin reagents, see: (a) Balas, L.; Jousseaume, B.; Shin, H.; Verlhac, J.-B.; Wallian, F. Organometallics 1991, 10, 366.
	(b) Jousseaume, B.; Kwon, H.; Verlhac, J.-B.; Denat, F.; Dubac, J. Synlett 1993,117.
	(c) Murakami, M.; Hoshino, Y.; Ito, H.; Ito, Y. Chem. Lett. 1998,163.
	(d) Hu, W.; Zheng, J.; Li, M.; Wu, W.; Liu, H.; Jiang, H. Chin. J. Chem. 2018, 36, 712.
[4]	Lemoucheux, L.; Rouden, J.; Lasne, M.-C. Tetrahedron Lett. 2000, 41, 9997.
[5]	Rieke, R. D.; Kim, S.-H. Tetrahedron Lett. 2012, 53, 3478.
[6]	Lysén, M.; Kelleher, S.; Begtrup, M.; Kristensen, J. L. J. Org. Chem. 2005, 70, 5342. pmid: 15960546
[7]	Duan, Y.-Z.; Deng, M.-Z. Synlett 2005,355.
[8]	Yasui, Y.; Tsuchida, S.; Miyabe, H.; Takemoto, Y. J. Org. Chem. 2007, 72, 5898. pmid: 17580905
[9]	Krishnamoorthy, R.; Lam, S. Q.; Manley, C. M.; Herr, R. J. J. Org. Chem. 2010, 75, 1251. pmid: 20088577
[10]	Kochi, T.; Urano, S.; Seki, H.; Mizushima, E.; Sato, M.; Kakiuchi, F. J. Am. Chem. Soc. 2009, 131, 2792. pmid: 19209853
[11]	(a) Matsuzono, M.; Fukuda, T.; Iwao, M. Tetrahedron Lett. 2001, 42, 7621. pmid: 17602463
	(b) Chao, W.-R.; Yean, D.; Amin, K.; Green, C.; Jong, L. J. Med. Chem. 2007, 50, 3412. pmid: 17602463
[12]	Lemoucheux, L.; Seitz, T.; Rouden, J.; Lasne, M.-C. Org. Lett. 2004, 6, 3703. pmid: 15469328
[13]	Selected reviews, see: (a) Baudoin, O. Angew. Chem., Int. Ed. 2007, 46, 1373. pmid: 28266216
	(b) Gooβen, L. J.; Rodriguez, N.; Gooβen, K. Angew. Chem.. Int. Ed. 2008, 47, 3100. pmid: 28266216
	(c) Rodríguez, N.; Gooβen, L. J. Chem. Soc. Rev. 2011, 40, 5030. pmid: 28266216
	(d) Dzik, W. I.; Lange, P. P.; Gooβen, L. J. Chem. Sci. 2012, 3, 2671. pmid: 28266216
	(e) Wei, Y.; Hu, P.; Zhang, M.; Su, W. Chem. Rev. 2017, 117, 8864. pmid: 28266216
[14]	Selected examples, see: (a) Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250. pmid: 16028944
	(b) Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323. pmid: 16028944
[15]	Gooßen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662. pmid: 16888137
[16]	(a) Gooßen, L. J.; Linder, C.; Rodriguez, N.; Lange, P. P.; Fromm, A. Chem. Commun. 2009,7173.
	(b) Cornella, J.; Sanchez, C.; Banawa, D.; Larrosa, I. Chem. Commun. 2009,7176.
[17]	(a) Cornella, J.; Rosillo-Lopez, M.; Larrosa, I. Adv. Synth. Catal. 2011, 353, 1359. doi: 10.1002/adsc.201100109
	(b) Dupuy, S.; Lazreg, F.; Slawin, A. M. Z.; Cazin, C. S. J.; Nolan, S. P. Chem. Commun. 2011, 47, 5455.
[18]	Sun, Z.-M.; Zhao, P. Angew. Chem., Int. Ed. 2009, 48, 6726.
[19]	Shang, R.; Fu, Y.; Wang, Y.; Xu, Q.; Yu, H.-Z.; Liu, L. Angew. Chem., Int. Ed. 2009, 48, 9350.
[20]	(a) Jiao, J.; Zhang, X.-R.; Chang, N.-H.; Wang, J.; Wei, J.-F.; Shi, X.-Y.; Chen, Z.-G. J. Org. Chem. 2011, 76, 1180. pmid: 20583793
	(b) Iwai, T.; Fujihara, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc. 2010, 132, 9602. pmid: 20583793
[21]	Yamasaki, R.; Morita, K.; Iizumi, H.; Ito, A.; Fukuda, K.; Okamoto, I. Chem.-Eur. J. 2019, 25, 10118. pmid: 31050845
[22]	Allah, T. N.; ne Savourey, S.; Berthet, J.-C.; Nicolas, E.; Cantat, T. Angew. Chem., Int. Ed. 2019, 58, 10884.
[23]	Song, G.; Sun, G.; Tang, Y.; Mai, W. J. Chem. Res. 2013,630.
[24]	Zhou, Y.; Zhang, X.; Zhang, Y.; Ruan, L.; Zhang, J.; Zhang-Negrerie, D.; Du, Y. Org. Lett. 2017, 19, 150. pmid: 28001422
[25]	Zhang, Z.; Liu, Y.-H.; Zhang, X.; Wang, X.-C. Tetrahedron 2019, 75, 2763.
[26]	Bao, Y.-S.; Zhaorigetu, B.; Agula, B.; Baiyin, M.; Jia, M. J. Org. Chem. 2014, 79, 803. pmid: 24364763
[27]	Ackermann, L.; Vicente, R.; Hofmann, N. Org. Lett. 2009, 11, 4274. doi: 10.1021/ol901597d pmid: 19775182
[28]	Das, K. G.; Funke, P. T.; Bose, A. K. J. Am. Chem. Soc. 1964, 86, 3729.

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

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 28

Related Articles 15

Recommended Articles

Metrics

Comments

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

[1]	Yang Li, Yanan Dong, Yuehui Li. Efficient Synthesis of Nitrile Compounds through Amide Conversion via N-Boroamide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 638-643.
[2]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[3]	Baochang Gao, Yu Shi, Yuan Tian, Zhiguo Zhang, Jingru Zhang, Yufeng Sun, Guoliang Mao, Lingyan Dai. Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 644-649.
[4]	Suyan Tao, Zixin Xiang, Junjie Bai, Xiao Wan, Xiaobing Wan. Amide Hydrolysis Reaction Using tert-Butyl Nitrite [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 550-560.
[5]	Gangzhong Jiang, Jiaxing Lin, Xiaoguang Bao, Xiaobing Wan. Isoamyl Nitrite Activated Primary Sulfonamide to Sulfonyl Bromide and Sulfonyl Chloride [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 533-549.
[6]	Zhiyou Huang, Ping Yang, Bo He, Wenxia Ou, Siyu Yuan. Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 309-315.
[7]	Lijun Xu, Zongjun Li, Fushe Han, Xiang Gao. N,N-Dimethylformamide-Promoted Synthesis of Fullerene-Fused Oxazoline Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 242-250.
[8]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[9]	Jing Tang, Wenkun Luo, Jun Zhou. Advances in the Synthesis of Azaspiro[4.5]trienones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3006-3034.
[10]	Xiao Song, Jing Qing, Jun Li, Xuelei Jia, Fusong Wu, Junrong Huang, Jian Jin, Hengzhi You. Copper-Catalyzed Asymmetric Allyl Alkylation Using Grignard Reagents under Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3174-3179.
[11]	Wenfeng Bei, Jian Pan, Dongmei Ran, Yilin Liu, Zhen Yang, Ruokun Feng. Cobalt-Catalyzed [4+2] Annulation of Indole Carboxamide with Diynes and Monoacetylene: Direct Access to γ-Carbolinones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3226-3238.
[12]	Jiaxia Pu, Xiaoying Jia, Lirong Han, Qinghan Li. Research Progress of Visible Light Promoted C—N Bond Fracture to Construct C—C Bond [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2591-2613.
[13]	Yu Wang, Yifang Chen, Xin Luo, Zhifu Xing, Ju Peng, Jixiang Chen. Design, Synthesis and Nematicidal Activity of Novel 2-Cyanoacrylate (Amide) Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2206-2216.
[14]	Zhijun Ren, Weiwei Luo, Jun Zhou. Recent Progress in Silver-Mediated Tandem Cyclization of N-Arylacrylamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2026-2039.
[15]	Wenhan Yang, Jiwen Jiao, Xiaoming Wang. Merging Electron Transfer Activation with 1,2-Metalate Migration: Deoxygenative Silylation of Amides [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1857-1867.