Citation: 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. doi: 10.6023/cjoc202006030 shu

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

Corresponding author: Xie Jianwei, cesxjw@foxmail.com Gong Shaofeng, simon.gong@huse.edu.cn
Received Date: 17 June 2020
Revised Date: 13 July 2020
Available Online: 30 July 2020
Fund Project: the National Natural Science Foundation of China 21868032the Opening Foundation of Engineering Research Center of Materials-Oriented Chemical Engineering of Xinjiang Bingtuan 2019BTRC001Project 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)

Figures(4)

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.
- decarboxylative amidation,
- primary amides,
- diphenylphosphoryl azide,
- α-keto acids,
- transition-metal-free
1. [1]
  Zabicky, J. The Chemistry of Amides, John-Wiley & Sons, Chichester, 1970.
2. [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. [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. [4]
  (a) Gooíen, L. J.; Rodríguez, N.; Gooíen, 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. [5]
  (a) Gooíen, 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. [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. [7]
  Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, R.; Qi, X.; Lan, Y.; Lei, A. Angew. Chem., Int. Ed. 2014, 53, 502. doi: 10.1002/anie.201308614
8. [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. [9]
  Xu, N.; Liu, J.; Li D.; Wang, L. Org. Biomol. Chem. 2016, 14, 4749. doi: 10.1039/C6OB00676K
10. [10]
  Pimpasri, C.; Sumunnee, L.; Yotphan, S. Org. Biomol. Chem. 2017, 15, 4320. doi: 10.1039/C7OB00776K
11. [11]
  Ilangovan, A.; Sakthivel, P.; Sakthivel, P. Org. Chem. Front. 2016, 3, 1680. doi: 10.1039/C6QO00343E
12. [12]
  (a) Wang, N.; Ma, P.; Xie, J.; Zhang, J. Mol. Diversity 2020, DOI:http://dx.doi.org/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. [13]
  Wadhwa, K.; Yang, C.; West, P. R.; Deming, K. C.; Chemburkar, S. R.; Reddy, R. E. Synth. Commun. 2008, 38, 4434. doi: 10.1080/00397910802369554
14. [14]
  Li, Y.; Chen, H.; Liu, J.; Wan, X. and Xu, Q. Green Chem. 2016, 18, 4865. doi: 10.1039/C6GC01565D
15. [15]
  Dubey, P.; Gupta, S.; Singh, A. K. Dalton Trans. 2017, 46, 13065. doi: 10.1039/C7DT02592K
16. [16]
  Ray, R.; Hazari, A. S.; Chandra, S.; Maiti, D.; Lahiri, G. K. Chem.-Eur. J. 2018, 24, 1067. doi: 10.1002/chem.201705601
17. [17]
  Deng, T.; Wang, C.-Z. ChemCatChem 2017, 9, 1349. doi: 10.1002/cctc.201700016
18. [18]
  Ribeiro, R. S.; Esteves, P. M.; Mattos, M. C. S. Synthesis 2011, 739.
19. [19]
  Li, X.-Q.; Wang, W.-K.; Han, Y.-X.; Zhang, C. Adv. Synth. Catal. 2010, 352, 2588. doi: 10.1002/adsc.201000318
20. [20]
  Gowda, R. R.; Chakraborty, D, Eur. J. Org. Chem. 2011, 2226.
21. [21]
  Allam, B. K.; Singh, K. N. Tetrahedron Lett. 2011, 52, 5851. doi: 10.1016/j.tetlet.2011.08.150
22. [22]
  Jaita, S.; Phakhodee, W.; Chairungsi, N.; Pattarawarapan, M. Tetrahedron Lett. 2018, 59, 3571. doi: 10.1016/j.tetlet.2018.08.035
1. [1]
  Pengfei Zhang , Qingxue Ma , Zhiwei Jiang , Xiaohua Xu , Zhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361
2. [2]
  Jindong Hao , Yufen Lv , Shuyue Tian , Chao Ma , Wenxiu Cui , Huilan Yue , Wei Wei , Dong Yi . Additive-free synthesis of β-keto phosphorodithioates via geminal hydro-phosphorodithiolation of sulfoxonium ylides with P₄S₁₀ and alcohols. Chinese Chemical Letters, 2024, 35(9): 109513-. doi: 10.1016/j.cclet.2024.109513
3. [3]
  Boqiang Wang , Yongzhuo Xu , Jiajia Wang , Muyang Yang , Guo-Jun Deng , Wen Shao . Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines. Chinese Chemical Letters, 2024, 35(9): 109502-. doi: 10.1016/j.cclet.2024.109502
4. [4]
  Tian Yang , Yi Liu , Lina Hua , Yaoyao Chen , Wuqian Guo , Haojie Xu , Xi Zeng , Changhao Gao , Wenjing Li , Junhua Luo , Zhihua Sun . Lead-free hybrid two-dimensional double perovskite with switchable dielectric phase transition. Chinese Chemical Letters, 2024, 35(6): 108707-. doi: 10.1016/j.cclet.2023.108707
5. [5]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
6. [6]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
7. [7]
  Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334
8. [8]
  Yatian Deng , Dao Wang , Jinglan Cheng , Yunkun Zhao , Zongbao Li , Chunyan Zang , Jian Li , Lichao Jia . A new popular transition metal-based catalyst: SmMn₂O₅ mullite-type oxide. Chinese Chemical Letters, 2024, 35(8): 109141-. doi: 10.1016/j.cclet.2023.109141
9. [9]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
10. [10]
  Shuanglin TIAN , Tinghong GAO , Yutao LIU , Qian CHEN , Quan XIE , Qingquan XIAO , Yongchao LIANG . First-principles study of adsorption of Cl₂ and CO gas molecules by transition metal-doped g-GaN. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1189-1200. doi: 10.11862/CJIC.20230482
11. [11]
  Zhen Dai , Linzhi Tan , Yeyu Su , Kerui Zhao , Yushun Tian , Yu Liu , Tao Liu . Site-specific incorporation of reduction-controlled guest amino acids into proteins for cucurbituril recognition. Chinese Chemical Letters, 2024, 35(5): 109121-. doi: 10.1016/j.cclet.2023.109121
12. [12]
  Hongmei Yu , Baoxi Zhang , Meiju Liu , Cheng Xing , Guorong He , Li Zhang , Ningbo Gong , Yang Lu , Guanhua Du . Theoretical and experimental cocrystal screening of temozolomide with a series of phenolic acids, promising cocrystal coformers. Chinese Chemical Letters, 2024, 35(5): 109032-. doi: 10.1016/j.cclet.2023.109032
13. [13]
  Liangji Chen , Zhen Yuan , Fudong Feng , Xin Zhou , Zhile Xiong , Wuji Wei , Hao Zhang , Banglin Chen , Shengchang Xiang , Zhangjing Zhang . A hydrogen-bonded organic framework containing fluorescent carbazole and responsive pyridyl units for sensing organic acids. Chinese Chemical Letters, 2024, 35(9): 109344-. doi: 10.1016/j.cclet.2023.109344
14. [14]
  Yanjing Li , Jiayin Li , Yuqi Chang , Yunfeng Lin , Lei Sui . Tetrahedral framework nucleic acids promote the proliferation and differentiation potential of diabetic bone marrow mesenchymal stem cell. Chinese Chemical Letters, 2024, 35(9): 109414-. doi: 10.1016/j.cclet.2023.109414
15. [15]
  Chunxiu Yu , Zelin Wu , Hongle Shi , Lingyun Gu , Kexin Chen , Chuan-Shu He , Yang Liu , Heng Zhang , Peng Zhou , Zhaokun Xiong , Bo Lai . Insights into the electron transfer mechanisms of peroxydisulfate activation by modified metal-free acetylene black for degradation of sulfisoxazole. Chinese Chemical Letters, 2024, 35(8): 109334-. doi: 10.1016/j.cclet.2023.109334
16. [16]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
17. [17]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
18. [18]
  Xinxiu Yan , Xizhe Huang , Yangyang Liu , Weishang Jia , Hualin Chen , Qi Yao , Tao Chen . Hyperbranched polyamidoamine protective layer with phosphate and carboxyl groups for dendrite-free Zn metal anodes. Chinese Chemical Letters, 2024, 35(10): 109426-. doi: 10.1016/j.cclet.2023.109426
19. [19]
  Yunfei Shen , Long Chen . Gradient imprinted Zn metal anodes assist dendrites-free at high current density/capacity. Chinese Journal of Structural Chemistry, 2024, 43(10): 100321-100321. doi: 10.1016/j.cjsc.2024.100321
20. [20]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244

Get Citation

PDF

XML

Metrics

PDF Downloads(51)
Abstract views(3030)
HTML views(332)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142