综述与进展

芳基三氮烯作为芳基前体和芳基偶氮前体在有机合成中的应用研究进展

  • 张永红 ,
  • 唐承宗 ,
  • 刘永红 ,
  • 刘晨江
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  • a 新疆大学化学学院 省部共建碳基能源资源化学与利用国家重点实验室 石油天然气精细化工教育部&自治区重点实验室 乌鲁木齐绿色催化与合成技术重点实验室 乌鲁木齐 830046
    b 北京分子科学国家研究中心 北京 100871

收稿日期: 2021-02-02

  修回日期: 2021-03-23

  网络出版日期: 2021-04-16

基金资助

新疆维吾尔自治区自然科学基金(2017D01C035); 国家自然科学基金(21762041); 国家自然科学基金(21861036)

Research Progress of Aryltriazene as Aryl Precursor and Aryl-Azo Precursors in Organic Synthesis

  • Yonghong Zhang ,
  • Chengzong Tang ,
  • Yonghong Liu ,
  • Chenjiang Liu
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  • a State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830046
    b Beijing National Laboratory for Molecular Sciences, Beijing 100871
* Corresponding authors. E-mail: ;

Received date: 2021-02-02

  Revised date: 2021-03-23

  Online published: 2021-04-16

Supported by

Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2017D01C035); National Natural Science Foundation of China(21762041); National Natural Science Foundation of China(21861036)

摘要

芳基三氮烯因制备简单, 稳定性好, 反应位点多, 反应条件温和等优点, 作为一种稳定的芳基重氮盐替代物被广泛用于有机合成中. 主要综述了近年来以芳基三氮烯作为芳基前体和芳基偶氮前体在有机合成中的应用研究进展.

本文引用格式

张永红 , 唐承宗 , 刘永红 , 刘晨江 . 芳基三氮烯作为芳基前体和芳基偶氮前体在有机合成中的应用研究进展[J]. 有机化学, 2021 , 41(7) : 2587 -2600 . DOI: 10.6023/cjoc202102014

Abstract

Aryltriazenes have been widely used as a stable aryldiazonium salt surrogate in organic synthesis, in which the compounds show advantages of easy preparation, good stability, multiple reaction sites and mild reaction conditions. In this review, the recent advances in the application of aryltriazenes in organic synthesis as aryl or aryl azo precursors are reviewed.

参考文献

[1]
(a) Rouzer,C. A.; Sabourin, M.; Skinner,T. L.; Thompson,E. J.; Wood,T. O.; Chmurny,G. N.; Klose,J. R.; Roman,J. M.; Smith,R. H.; Michejda,C. J. Chem. Res. Toxicol. 1996, 9,172.
[1]
(b) Gross,M. L.; Blank,D. H.; Welch,W. M. J. Org. Chem. 1993, 58,2104.
[2]
Griess, P. Justus Liebigs Ann. Chem. 1862, 121,258.
[3]
Connors,T. A.; Goddard,P. M.; Merai, K.; Ross,W. C.J.; Wilman,D. E.V. Biochem. Pharmacol. 1976, 25,241.
[4]
Li, Q.; Jin, C.; Petukhov,P. A.; Rukavishnikov,A. V.; Zaikova,T. O.; Phadke, A.; LaMunyon,D. H.; Lee,M. D.; Keana,J. F.W. J. Org. Chem. 2004, 69,1010.
[5]
Romanato, P.; Duttwyler, S.; Linden, A.; Baldridge,K. K.; Siegel,J. S. J. Am. Chem. Soc. 2010, 132,7828.
[6]
Jenny,N. M.; Wang, H.; Neuburger, M.; Fuchs, H.; Chi, L.; Mayor, M. Eur. J. Org. Chem. 2012, 14,2738.
[7]
Romanato, P.; Duttwyler, S.; Linden, A.; Baldridge,K. K.; Siegel,J. S. J. Am. Chem. Soc. 2011, 133,11844.
[8]
Kirk,M. L.; Shultz,D. A.; Stasiw,D. E.; Lewis,G. F.; Wang, G.; Brannen,C. L.; Sommer,R. D.; Boyle,P. D. J. Am. Chem. Soc. 2013, 135,17144.
[9]
Romanato, P.; Duttwyler, S.; Linden, A.; Baldridge,K. K.; Siegel,J. S. J. Phys. Org. Chem. 2014, 27,277.
[10]
Xue, D.; Luo,S. -P.; Zhan,S. -Z. New J. Chem. 2017, 41,8503.
[11]
Kimball,D. B.; Haley,M. M. Angew. Chem. Int. Ed. 2002, 41,3338.
[12]
(a) Zhang, Y.; Cao, D.; Liu, W.; Hu, H.; Zhang, X.; Liu, C. Curr. Org. Chem. 2015, 19,151.
[12]
(b) Botting,N. P.; Challis,B. C. J. Chem. Soc. Chem. Commun. 1989,1585.
[12]
(c) Lazny, R.; Poplawski, J.; Köbberling, J.; Enders, D.; Bräse, S. Synlett 1999,1304.
[13]
(a) Sousa, A.; Santos, F.; Gaspar,M. M.; Calado, S.; Pereira,J. D.; Mendes, E.; Francisco,A. P.; Perry,M. J. Bioorg. Med. Chem. 2017, 25,3900.
[13]
(b) Mouhri,Z. S.; Goodfellow, E.; Kelley,S. P.; Stein,R. S.; Rogers,R. D.; Jean-Claude,B. J. Molecules 2017, 22,1183.
[14]
Wang, Q.; Wang,C. -B.; Pang,F. -Q.; Lu, T.; Yin,H. -Q.; Chen,F. -X. Chin. Chem. Lett. 2017, 28,1784.
[15]
(a) Wang, Q.; Pang, F.; Wang, G.; Huang, J.; Nie, F.; Chen, F. Chem. Commun. 2017, 53,2327.
[15]
(b) Khramov,D. M.; Bielawski,C. W. J. Org. Chem. 2007, 72,9407.
[16]
(a) Sieh,D. H.; Wilbur,D. J.; Michejda,C. J. J. Am. Chem. Soc. 1980, 102,3883.
[16]
(b) Nakhai, A.; Stensland, B.; Svensson,P. H.; Bergman, J. Eur. J. Org. Chem. 2010, 34,6588.
[16]
(c) Suleymanov,A. A.; Scopelliti, R.; Tirani,F. F.; Severin, k. Org. Lett. 2018, 20,3323.
[17]
Kiefer, G.; Riedel, T.; Dyson,P. J.; Scopelliti, R.; Severin, K. Angew. Chem. Int. Ed. 2015, 54,302.
[18]
(a) Tan,J. -F.; Bormann,C. T.; Perrin,F. G.; Chadwick,F. M.; Severin, K.; Cramer, N. J. Am. Chem. Soc. 2019, 141,10372.
[18]
(b) Wezeman, T.; Scopelliti, R.; Tirani,F. F.; Severin, K. Adv. Synth. Catal. 2019, 361,1383.
[19]
(a) Fanghänel, E.; Poleschner, H.; Radelgia, R.; Hänsel, R. J.Prakt. Chem. 1977, 319,813.
[19]
(b) Nguyen,M. T.; Hoesch, L. Helv. Chim. Acta 1986, 69,1627.
[19]
(c) Schmiedekamp, A.; Smith,R. H.; Michejda,C. J. J. Org. Chem. 1988, 53,3433.
[19]
(d) Fanghänel E.; Ortmann W. J. Prakt. Chem. 1989, 331,721.
[19]
(e) Ozment,J. L.; Schmiedekamp,A. M.; Schultz-Merkel,L. A.; Smith,R. H.; Michejda,C. J. J. Am. Chem. Soc. 1991, 113,397.
[19]
(f) Schmiedekamp,A. M.; Topol,I. A.; Burt,S. K.; Razafinjanahary, H.; Chermette, H.; Pfaltzgraff, T.; Michejda,C. J. J. Comput. Chem. 1994, 15,875.
[19]
(g) Rakotondradany, F.; Williams,C. I.; Whitehead,M. A.; Jean-Claude,B. J. J. Mol. Struct.:THEOCHEM 2001, 535,217.
[19]
(h) Kimani,F. W.; Jewett,J. C. Angew. Chem. Int. Ed. 2015, 54,4051.
[20]
Landman,I. R.; Suleymanov,A. A.; Fadaei-Tirani, F.; Scopelliti, R.; Chadwick,F. M.; Severin, K. Dalton Trans. 2020, 49,2317.
[21]
Bhattacharya, S.; Majee, S.; Mukherjee, R.; Sengupta, S. Synth. Commun. 1995, 25,651.
[22]
Sengupta, S.; Sadhukkan,S. K. Tetrahedron Lett. 1998, 39,715.
[23]
Bräse, S.; Schroen, M. Angew. Chem. Int. Ed. 1999, 38,1071.
[24]
Kumar, S.; Pandey,A. K.; Singh, R.; Singh,K. N. Eur. J. Org. Chem. 2018, 43,5942.
[25]
Sutar,S. M.; Savanur,H. M.; Malunavar,S. S.; Prabhala, P.; Kalkhambkar,R. G.; Laali,K. K. Eur. J. Org. Chem. 2019,6088.
[26]
Vishwakarma,R. K.; Kumar, S.; Sharma,A. K.; Singh, R.; Singh,K. N. ChemistrySelect 2019, 4,4064.
[27]
Saeki, T.; Son,E. C.; Tamao, K. Org. Lett. 2004, 6,617.
[28]
Liu,C. -Y.; Gavryushin, A.; Knochel, P. Chem. Asian J. 2007, 2,1020.
[29]
Nan, G.; Ren F.; Luo, M. Beilstein J. Org. Chem. 2010, 6, No.70. doi: 10.3762/bjoc.6.70.
[30]
Nan, G.; Zhu, F.; Wei, Z. Chin. J. Chem. 2011, 29,72.
[31]
Nan, G..; Zhou, J. Chin. J. Org. Chem. 2012, 32,1695 (in Chinese).
[31]
( 南光明, 周均, 有机化学, 2012, 32,1695.)
[32]
Nan,G. M.; Zhou, J.; Yan,W. L. Asian J. Chem. 2013, 25,10322.
[33]
Mao, S.; Chen, Z.; Wang, L.; Khadka, D.; Xin, M.; Li, P.; Zhang, S. J. Org. Chem. 2019, 84,463.
[34]
Sengupta, S.; Sadhukkan,S. K. Org. Synth. 2002, 79,52.
[35]
Saeki, T.; Matsunaga, T.; Son,E. C.; Tamao, K. Adv. Synth. Catal. 2004, 346,1689.
[36]
Zhou, J.; Yang,W. J.; Wang,B. J.; Ren,H. J. Angew. Chem. Int. Ed. 2012, 51,12293.
[37]
Xu, L.; Yang, W.; Zhang, L.; Miao, M.; Yang, Z.; Xu, X.; Ren, H. J. Org. Chem. 2014, 79,9206.
[38]
Liu, C.; Miao, T.; Zhang, L.; Li, P..; Zhang, Y.; Wang, L. Chem. Asian J. 2014, 9,2584.
[39]
Wang, R.; Falck,J. R. Org. Chem. Front. 2014, 1,1029.
[40]
Chaubey,N. R.; Vishwakarma,R. K.; Singh,K. N. ChemistrySelect 2019, 4,8522.
[41]
Zificsak,C. -A.; Hlasta,D. -J. Tetrahedron 2004, 60,8991.
[42]
Dai,W. C.; Wang,Z. X. Org. Chem. Front. 2017, 4,1281.
[43]
Liu, C.; Wang, Z.; Wang, L.; Li, P.; Zhang, Y. Org. Biomol. Chem. 2019, 17,9209.
[44]
Barragan, E.; Poyil,A. N.; Yang,C. -H.; Wang, H.; Bugarin, A. Org. Chem. Front. 2019, 6,152.
[45]
Li, W.; Wu,X. -F. Org. Biomol. Chem. 2015, 13,5090.
[46]
Li, W.; Wu,X. F. Org. Lett. 2015, 17,1910.
[47]
Yin, Z.; Wang, Z.; Wu,X. -F. Eur. J. Org. Chem. 2017,3992.
[48]
Yin, Z.; Wang, Z.; Wu,X. -F. Org. Lett. 2017, 19,6232.
[49]
Chand, S.; Kumar, S.; Singh, R.; Singh,K. N.; ChemistrySelect 2019, 4,718.
[50]
Wippert,N. A.; Jung, N.; Bräse, S. ACS Comb. Sci. 2019, 21,568.
[51]
Barragan, E.; Noonikara-Poyil, A.; Bugarin, A. Asian J. Org. Chem. 2020, 9,593.
[52]
Khazaei, A.; Kazem-Rostami, M.; Moosavi-Zare,A. R.; Bayat, M.; Saednia, S. Synlett 2012, 23,1893.
[53]
Zhang, Y.; Li, Y.; Zhang, X.; Jiang, X. Chem. Commun. 2015, 51,941.
[54]
Pandey,A. K.; Chand, S.; Singh, R.; Kumar, S.; Singh,K. N. ACS Omega 2020, 5,7627.
[55]
Pandey,A. K.; Kumar, S.; Singh, R.; Singh,K. N. Tetrahedron 2018, 74,6704.
[56]
Qi,X. -X.; Jiang,L. -B.; Zhou, C.; Peng,J. -B.; Wu,X. -F. ChemistryOpen 2017, 6,345.
[57]
Kimball,D. B.; Hayes,A. G.; Haley,M. M. Org. Lett. 2000, 2,3825.
[58]
(a) Kimball,D. B.; Herges, R.; Haley,M. M. J. Am. Chem. Soc. 2002, 124,1572.
[58]
(b) Kimball,D. B.; Weakley,T. J.R.; Haley,M. M. J. Org. Chem. 2002, 67,6395.
[59]
Zhu, C.; Yamane, M. Tetrahedron 2011, 67,4933.
[60]
Yang, W.; Yang, Z.; Xu, L.; Zhang, L.; Xu, X.; Miao, M.; Ren, H. Angew. Chem. Int. Ed. 2013, 52,14135.
[61]
Wang, D.; Cui, S. Tetrahedron 2016, 72,2725.
[62]
Cao, D.; Zhang, Y.; Liu, C.; Wang, B; Sun, Y.; Abdukadera, A.; Hu, H.; Liu, Q. Org. Lett. 2016, 18,2000.
[63]
Zhang, Y.; Hu, H.; Liu, C.; Cao, D.; Wang, B.; Sun, Y.; Abdukader, A. Asian J. Org. Chem. 2017, 6,102.
[64]
Zhang, Y.; Liu, Y.; Ma, X.; Ma, X.; Wang, B.; Li, H.; Huang, Y.; Liu, C. Dyes Pigm. 2018, 158,438.
[65]
Liu, Y.; Ma, X.; Wu, G.; Liu, Z.; Yang, X.; Wang, B.; Liu, C.; Zhang, Y.; Huang, Y. New J. Chem. 2019, 43,9255.
[66]
Liu, C.; Lv, J.; Luo,S. Z.; Cheng,J. P. Org. Lett. 2014, 16,5458.
[67]
Sheng, M.; Frurip, D.; Gorman, D. J. Loss Prev. Process Ind. 2015, 38,114.
[68]
Firth,J. D.; Fairlamb,I. J.S. Org. Lett. 2020, 22,7057.
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