Citation: Sheng Rong, Li Ping, Zhou Zhiqiang, Hu Guiwen, Zhang Xiaoxiang. Pd-Catalyzed One-Pot Oxidation/Hydrolysis for the Synthesis of 2-Benzoylaminobenzoic Acids from 2-Alkynyl Arylazides[J]. Chinese Journal of Organic Chemistry, ;2020, 40(2): 462-469. doi: 10.6023/cjoc201909005 shu

Pd-Catalyzed One-Pot Oxidation/Hydrolysis for the Synthesis of 2-Benzoylaminobenzoic Acids from 2-Alkynyl Arylazides

  • Corresponding author: Zhang Xiaoxiang, zhangxiaoxiang@njfu.edu.cn
  • Received Date: 2 September 2019
    Revised Date: 27 September 2019
    Available Online: 12 February 2019

    Fund Project: the National Natural Science Foundation of China No. 21302096the Natural Science Foundation of Jiangsu Province No. BK20171449Project supported by the Postgraduate Research & Practice Innovation Program of Jiangsu Province (No. KYCX18_0967), the National Natural Science Foundation of China (No. 21302096), the Natural Science Foundation of Jiangsu Province (No. BK20171449) and the Qing Lan ProjectProject supported by the Postgraduate Research & Practice Innovation Program of Jiangsu Province No. KYCX18_0967

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  • A synthetic method to prepare 2-benzoylaminobenzoic acids via Pd-catalyzed one-pot oxidation/hydrolysis from 2-alkynyl arylazides is described. The reaction was accomplished in good to excellent yields under mild reaction conditions.
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    1. [1]

      (a) Gurure R., Atkinson J., Moccia R...Aquacult. Nutr. 2007, 13, 266. (b) Concepcion. C.; Claudia S. M...J. Food. Sci. 1993, 58, 1324. (c) Duan Y., Chen X., Shao Z. Z...Acta Chim. Sinica 2018, 76, 190 (in Chinese).(d) Bi J...l.; Ma R. S...Yang J. H...Chin. J. Org. Chem. 2018, 38, 2553 (in Chinese). (e) Shi K. J., Yu B., Long L. S., Shun Y. L., Wen H. H...Chin. Chem. Lett. 2016, 28, 213.

    2. [2]

      (a) Yellaiah T., Kesari L. M., Manda S., Abdullah A., Ahmed K...Asian J. Org. Chem. 2017, 6, 898. (b) Wu W., Woodie P...W; James C., Yun H., Foster B. W., Lawrence W. G...J. Agric. Food. Chem. 1996, 44, 1296. (c) Santosh N. M., Akash D. P., Pritam N. D., Nikhil S. S., Pankaj B. M...Bioorg. Med. Chem. Lett. 2016, 26, 272. (d) Wei L., Irshad A. B., Hui J. S., Chang J. C., Rui G..., In P. J., Di W., Mei D., Moon Y. Y., Jian G. W...Eur. J. Med. Chem. 2015, 94, 298. (e) Arghya B., Sourav K. S., Prakash R...Mo.; Bhisma K. P...Org. Lett. 2015, 17, 5678. (f) Guo L., Ramesh K., Samuel W. G., Annapurna P., Bao Q. M...Tetrahedron Lett. 2009, 50, 6048. (g) Elisabeth W., Johannes C. D. J., Christian B., Michael P. S., Andrea B., Matthias N.; Alberto P.; Anke S., Rolf M., Rolf W. H...J. Med. Chem. 2013, 56, 6146.

    3. [3]

      (a) Stefan H., Kristina H., Matthias G., Matthias N., Jorg H., Rolf W. H...J. Med. Chem. 2013, 56, 8332. (b) Stanislav G., Petra B., Tea L. R...Bioorg. Med. Chem. Lett. 2005, 15, 5170. (c) Christopher T. W., Stuart W. H., Brian D. A., Xue G., Yi Tang. ACS Chem. Biol. 2013, 8, 1366.

    4. [4]

      For selected examples on the synthesis of 2-benzamidobenzoic acids, see: (a) Miklos C., Gabor S., Jozsef K., Nadia E. B., Etelka F...Tetrahedron 2013, 69, 6666. (b) Jozsef K., Tama C., Miklo C., Gabor S., Marius R., Michel G...Inorg. Chem. Commum. 2005, 8, 813. (c) Kuppusamy B., Thanasekaran P., Ahamed A. J...Eur. J. Org. Chem. 2017, 19, 2806. (d) Mitsuaki Y., Akira I...Tetrahedron 2014, 70, 5746. (e) Karima I. B., Baya B. K., Cherifa R., Malika M. C., Maamar H., Artur M. S. S...Molecules 2018, 23, 8.

    5. [5]

      Ramesh G., Jonathan K. L., Yu J.-Q...J. Am. Chem. Soc. 2010, 132, 686.  doi: 10.1021/ja9077705

    6. [6]

      (a) Yi N. W., Cheng J., De Y. W., Qiong G., Zhang Y. L., Hai B. L...Chem. Commun. 2016, 52, 1286. (b) Antonio A., Marco C., Luana D. V., Fabio M., Veronique M...Chem. Commum. 2016, 52, 1458. (c) P, Kumar.; M, Gupta.; V, Bahadur.; V S...Parmar.; B K...Singh. Eur. J. Org. Chem. 2018, 13, 1552.

    7. [7]

      Mitsuaki Y., Yukari, Ni.; Seiya H., Akira I...Tetrahedron 2016, 72, 4123.  doi: 10.1016/j.tet.2016.05.054

    8. [8]

      For our recent studies on transformation of 2-alkynyl arylazides via α-imino palladium carbenes, see: (a) Li P., Yong W. X., Sheng R., Rao W. D., Zhu X. B., Zhang X. X...Adv. Synth. Catal. 2019, 361, 201. (b) Zhang X. X., Li P., Yong W. X., Lyu C., Li J., Pan X. Y., Zhu X. B., Rao W. D...Adv. Synth. Catal. 2017, 23, 4147. (c) Zhang X. X., Li P., Yong W. X., Lyu C., Li J., Zhu X. B., Rao W. D...Org. Biomol. Chem. 2017, 15, 6080.

    9. [9]

      For recent selected examples on the generation of gold carbenes, see: (a) Chao S., Chong Y. S., Qing S., Bo Z., Tian Y. L., Qiao H., Xin L., Rai S. L., Long W. Y...ACS Catal. 2019, 9, 1019. (b) Ming B., Xin W., Li H. Q., Wen H. H., Philip W. H. C., Xin F. X...Org. Lett. 2019, 21, 1813. (c) Yi Z., Jian W. J., Philip W. H. C...Adv. Synth. Catal. 2019, 361, 1171. (d) Ji B. L., Pushkin C., Heng Z., Liang Z., Zhi X. W., Xue, L H...ACS Catal. 2019, 9, 2610.

    10. [10]

      For recent selected examples on the generation of α-imino gold or Pd carbenes, see: (a) Nan L., Xiao L. L., Yu H. L., Tian Y. W., Zhi Y...Ha. Li T. Z., Liu Z. G...Org. Lett. 2016, 18, 4178. (b) Hong M. J., Long H., Jin X., Matthias R., Frank R.; A. Stephen K. H. Angew. Chem. Int. Ed. 2016, 55, 794. (c) Rajkumar L. S., Rai S. L...Angew. Chem. Int. Ed. 2017, 56, 1026. (d) Geoffroy H. L., Ciputra T., Hui L. C., Shunsuke C., Fabien G. Chem. Commun. 2017, 53, 736. (e) Xian H. T., Lina S., Matthias R., Frank R. A...Stephen K. H. Org. Lett. 2019, 21, 4327. (f) Jian W. J., Yi C. Z., Ella M. L. S., Prasath K., Philip W. H. C...Adv. Synth. Catal. 2018, 360, 4744. (g) Hua L. D., Song L. B., Ping L., Yan G. W...Org. Lett. 2017, 19, 4604. (h) Wen H. W., Han M. H...Chem. Commun. 2019, 55, 3947. (i) Yi F. P., Tai W. C., Kang W., Jing F. H., Jian B. W...Chem. Commun. 2019, 55, 59. (j) Zhen X. L., Jing F. H., Tian, R F.; Hao C. T., Fei Y., Mohammad L. H., Jian B. W...Chem. Commun. 2018, 54, 11419.

    11. [11]

      For recent examples on the formation of 2-phenyl-3H-indol-3-one D, see: (a) Jin S. L., Yong J. L., Guang W. Z., Jun A. M...Org. Lett. 2017, 19, 6364. (b) Jin S. L., Yong J. L., Shen L., Jun A...Ma. Chem. Commun. 2018, 54, 9151. (c) Jin D...Z, Shuai S. F., Ke W. S., Chao F., Tao L., Ding D...J. Org. Chem. 2018, 83, 10430. (d) Jing X...L, Qing Q. Z., Jin G. D., Ying C. C...Org. Biomol. Chem. 2013, 11, 8175.

    12. [12]

      For recent examples on the synthesis of 4H-3, 1-benzoxazin-4-one E, see: (a) Qi L. L., Pin H. C., Guo S. L...ACS Catal. 2013, 3, 178. (b) Zhi P. Y., Ze C. W., Xiao F. W...Org. Lett. 2017, 19, 6232. (c) Ming L., Jian W...Org. Chem. Front. 2019, 6, 1367. (d) Long W., Yi B. X., Nian Y. H., Jia Y. Y., Wei M. H., Ming G. L., Ming W. D...ACS Catal. 2016, 6, 4010. (e) Wei L. C., Si Y. W., Xue L. M., Liu X. W., Cui L., Dong L. M...Org. Lett. 2018, 20, 3527. (f) Zhang X. X., Lü C., Li P., Yong W. X., Li J., Zhu X. B...Chin. J. Org. Chem. 2018, 38, 208 (in Chinese).(g) Zhou P. P., Guan M. Y., Zhang J. Y., Xu F., Zhao Y. S...Chin. J. Org. Chem. 2017, 37, 2028 (in Chinese).

    13. [13]

      (a) Timo H., Srinath T., Matthew D., Mark R. P., Glenn M., Colin W. G. F., Peter J...Bioorg. Med. Chem. Lett. 2006, 16, 88. (b) Nagahisa Y., Kenji M., Hidehiko K., Akihisa M., Takashi D., Tetsuo N., Toshio M., Kanji M...Bioorg. Med. Chem. Lett. 2018, 28, 809.

    14. [14]

      (a) Stefan H., Johannes C. D. J..., Matthias G., Jorg H., Rolf W. H...Eur. J. Med. Chem. 2014, 76, 343. (b) Zhe N., Carin P., Jia L., Ying S., Stephen M., Ketan S. G., Joseph C., Victor N., Kraig M. Y., Krzysztof A.; Shao S. C...J. Med. Chem. 2005, 48, 1596.

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