Transition-Metal-Free Decarboxylative Amidation of Aryl α-Keto Acids with Diphenylphosphoryl Azide: New Avenue for the Preparation of Primary Aryl Amides

doi:10.6023/cjoc202006030

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (12): 4284-4289.DOI: 10.6023/cjoc202006030 Previous Articles Next Articles

无过渡金属条件下α-芳香酮酸与叠氮磷酸二苯酯脱羧酰胺化制备芳香伯酰胺

谢建伟^a,b, 沈丽^b, 张洁^b, 龚绍峰^a

a 湖南科技学院化学与生物工程学院湖南永州 425199;
b 石河子大学化学化工学院新疆石河子 832003

收稿日期:2020-06-17 修回日期:2020-07-13 发布日期:2020-08-01
通讯作者: 谢建伟, 龚绍峰 E-mail:cesxjw@foxmail.com;simon.gong@huse.edu.cn
基金资助:
国家自然科学基金（No.21868032）和新疆兵团材料化工工程技术研究中心开放基金（No.2019BTRC001）资助项目.

Transition-Metal-Free Decarboxylative Amidation of Aryl α-Keto Acids with Diphenylphosphoryl Azide: New Avenue for the Preparation of Primary Aryl Amides

Xie Jianwei^a,b, Shen Li^b, Zhang Jie^b, Gong Shaofeng^a

a College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199;
b School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003

Received:2020-06-17 Revised:2020-07-13 Published:2020-08-01
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21868032) and the Opening Foundation of Engineering Research Center of Materials-Oriented Chemical Engineering of Xinjiang Bingtuan (No. 2019BTRC001).

1. cjoc202006030.pdf(1391KB)

Abstract

In this paper, a novel transition-metal-free decarboxylative amidation of aryl α-keto acids with diphenylphosphoryl azide (DPPA) under mild conditions has been developed. The reaction proceeded smoothly to afford the corresponding primary aryl amide products in good to excellent yields under air and showed excellent functional group tolerance. Gram-scale reaction was also performed to produce the desired product in high yield. In addition, the mechanism of the present reaction was investigated.

Key words: decarboxylative amidation, primary amides, diphenylphosphoryl azide, α-keto acids, transition-metal-free

Cite this article

Xie Jianwei, Shen Li, Zhang Jie, Gong Shaofeng. Transition-Metal-Free Decarboxylative Amidation of Aryl α-Keto Acids with Diphenylphosphoryl Azide: New Avenue for the Preparation of Primary Aryl Amides[J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4284-4289.

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[1] Zabicky, J. The Chemistry of Amides, John-Wiley & Sons, Chichester, 1970.
[2] Greenberg, A.; Breneman, C. M.; Liebman, J. F. The Amide Linkage:Structural Significance in Chemistry, Biochemistry and Material Science, Wiley, New York, 2000.
[3] For some selected reviews, see:(a) Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer Jr, J. J. L.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411.
(b) Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606.
(c) Allen, C. L.; Williams, J. M. J. Chem. Soc. Rev. 2011, 40, 3405.
(d) Kaiser, D.; Bauer, A.; Lemmerer, M.; Maulide, N. Chem. Soc. Rev. 2018, 47, 7899.
(e) de Figueiredo, R. M.; Suppo, J.-S.; Campagne, J.-M. Chem. Rev. 2016, 116, 12029.
(f) Dunetz, J. R.; Magano, J.; Weisenburger, G. A. Org. Process Res. Dev. 2016, 20, 140.
[4] (a) Gooßen, L. J.; Rodríguez, N.; Gooßen, K. Angew. Chem., Int. Ed. 2008, 47, 3100.
(b) Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030.
(c) Shang, R.; Liu, L. Sci. China:Chem. 2011, 54, 1670.
[5] (a) Gooßen, L. J.; Rudolphi, F.; Oppel, C.; Rodríguez, N. Angew. Chem., Int. Ed. 2008, 47, 3043.
(b) Shang, R.; Fu, Y.; Li, J.-B.; Zhang, S.-L.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738.
(c) Fang, P.; Li, M.; Ge, H. J. Am. Chem. Soc. 2010, 132, 11898.
(d) Li, M.; Ge, H. Org. Lett. 2010, 12, 3464.
(e) Miao, J.; Ge, H. Org. Lett. 2013, 15, 2930.
(f) Li, D.; Wang, M.; Liu, J.; Zhao, Q.; Wang, L. Chem. Commun. 2013, 49, 3640.
(g) Wang, C.; Wang, S.; Li, H.; Yan, J.; Chi, H.; Chen, X.; Zhang, Z. Org. Biomol. Chem. 2014, 12, 1721.
(h) Song, Q.; Feng, Q.; Yang, K. Org. Lett. 2014, 16, 624.
(i) Yan, K.; Yang, D.; Wei, W.; Zhao, J.; Shuai, Y.; Tian, L.; Wang, H. Org. Biomol. Chem. 2015, 13, 7323.
(j) Nanjo, T.; Kato, N.; Zhang, X.; Takemoto, Y. Chem.-Eur. J. 2019, 25, 15504.
(k) Jin, J.; Zhang, F.; Wang, Y. Acta Chim. Sinica 2019, 77, 889(in Chinese). (靳继康, 张凤莲, 汪义丰, 化学学报, 2019, 77, 889.)
[6] For some selected reviews and recent examples, see:(a) Weaver, J. D.; Recio III, A.; Grenning, A. J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846.
(b) Li, Z.; Jiang, Y.-Y.; Yeagley, A. A.; Bour, J. P.; Liu, L.; Chruma, J. J.; Fu, Y. Chem.-Eur. J. 2012, 18, 14527.
(c) Dzik, W. I.; Lange, P. P.; Gooßen, L. J. Chem. Sci. 2012, 3, 2671.
(d) Kim, M.; Park, J.; Sharma, S.; Kim, A.; Park, E.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Chem. Commun. 2013, 49, 925.
(e) Wang, H.; Guo, L.-N.; Duan, X.-H. Chem. Commun. 2014, 50, 7382.
(f) Liu, C.; Wang, X.; Li, Z.; Cui, L.; Li, C. J. Am. Chem. Soc. 2015, 137, 9820.
(g) Wang, H.; Zhou, S.-L.; Guo, L.-N.; Duan, X.-H. Tetrahedron 2015, 71, 630.
(h) Jiang, Q.; Jia, J.; Xu, B.; Zhao, A.; Guo, C.-C. J. Org. Chem. 2015, 80, 3586.
(i) Wu, Y.; Sun, L.; Chen, Y.; Zhou, Q.; Huang, J.-W.; Miao, H.; Luo, H.-B. J. Org. Chem. 2016, 81, 1244.
(j) Xie, L.-Y.; Peng, S.; Lu, L.-H.; Hu, J.; Bao, W.-H.; Zeng, F.; Tang, Z.; Xu, X.; He, W.-M. ACS Sustainable Chem. Eng. 2018, 6, 7989.
(k) Xie, L.-Y.; Hu, J.-L.; Song, Y.-X.; Jia, G.-K.; Lin, Y.-W.; He, J.-Y.; Cao, Z.; He, W.-M. ACS Sustainable Chem. Eng. 2019, 7, 19993.
(l) Penteado, F.; Lopes, E. F.; Alves, D.; Perin, G.; Jacob, R. G.; Lenardão, E. J. Chem. Rev. 2019, 119, 7113.
[7] Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, R.; Qi, X.; Lan, Y.; Lei, A. Angew. Chem., Int. Ed. 2014, 53, 502.
[8] (a) Xu, W.-T.; Huang, B.; Dai, J.-J.; Xu, J.; Xu, H.-J. Org. Lett. 2016, 18, 3114.
(b) Xu, X.-L.; Xu, W.-T; Wu, J.-W.; He, J.-B.; Xu, H.-J. Org. Biomol. Chem. 2016, 14, 9970.
[9] Xu, N.; Liu, J.; Li D.; Wang, L. Org. Biomol. Chem. 2016, 14, 4749.
[10] Pimpasri, C.; Sumunnee, L.; Yotphan, S. Org. Biomol. Chem. 2017, 15, 4320.
[11] Ilangovan, A.; Sakthivel, P.; Sakthivel, P. Org. Chem. Front. 2016, 3, 1680.
[12] (a) Wang, N.; Ma, P.; Xie, J.; Zhang, J. Mol. Diversity 2020, DOI:10. 1007/s11030-020-10058-6.
(b) Xie, J.; Wang, X.; Wu, F.; Zhang, J. Chin. J. Org. Chem. 2019, 39, 3026(in Chinese). (谢建伟, 汪小创, 吴丰田, 张洁, 有机化学, 2019, 39, 3026.)
(c) Xie, J.-W.; Yao, Z.-B.; Wang, X.-C.; Zhang, J. Tetrahedron 2019, 75, 3788.
(d) Shen, L.; Zhang, J.; Xie, J. Chin. J. Org. Chem. 2019, 39, 1153(in Chinese). (沈丽, 张洁, 谢建伟, 有机化学, 2019, 39, 1153.)
[13] Wadhwa, K.; Yang, C.; West, P. R.; Deming, K. C.; Chemburkar, S. R.; Reddy, R. E. Synth. Commun. 2008, 38, 4434.
[14] Li, Y.; Chen, H.; Liu, J.; Wan, X. and Xu, Q. Green Chem. 2016, 18, 4865.
[15] Dubey, P.; Gupta, S.; Singh, A. K. Dalton Trans. 2017, 46, 13065.
[16] Ray, R.; Hazari, A. S.; Chandra, S.; Maiti, D.; Lahiri, G. K. Chem.-Eur. J. 2018, 24, 1067.
[17] Deng, T.; Wang, C.-Z. ChemCatChem 2017, 9, 1349.
[18] Ribeiro, R. S.; Esteves, P. M.; Mattos, M. C. S. Synthesis 2011, 739.
[19] Li, X.-Q.; Wang, W.-K.; Han, Y.-X.; Zhang, C. Adv. Synth. Catal. 2010, 352, 2588.
[20] Gowda, R. R.; Chakraborty, D, Eur. J. Org. Chem. 2011, 2226.
[21] Allam, B. K.; Singh, K. N. Tetrahedron Lett. 2011, 52, 5851.
[22] Jaita, S.; Phakhodee, W.; Chairungsi, N.; Pattarawarapan, M. Tetrahedron Lett. 2018, 59, 3571.

无过渡金属条件下α-芳香酮酸与叠氮磷酸二苯酯脱羧酰胺化制备芳香伯酰胺

Transition-Metal-Free Decarboxylative Amidation of Aryl α-Keto Acids with Diphenylphosphoryl Azide: New Avenue for the Preparation of Primary Aryl Amides

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