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2023 , Vol. 43 >Issue 4: 1341 - 1364

DOI: https://doi.org/10.6023/cjoc202209007

综述与进展

基于C—CN键断裂的芳香腈转化反应研究进展

  • 缪存静 ,
  • 姚佳琪
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  • a 浙江大学医学院附属邵逸夫医院钱塘院区药学部 杭州 310018
    b 中国科学院大学宁波华美医院药学部 浙江宁波 315000

收稿日期: 2022-09-05

  修回日期: 2022-10-17

  网络出版日期: 2022-11-22

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Recent Advances in the Transformation Reactions of Aromatic Nitriles via C—CN Bond Cleavage

  • Cunjing Miao ,
  • Jiaqi Yao
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  • a Department of Pharmacy, Qiantang Campus, Sir Run Run Shaw Hospital, College of Medicine, Zhejiang University, Hangzhou, 310018
    b Department of Pharmacy, Ningbo Huamei Hospital, University of Chinese Academy of Sciences, Ningbo, Zhejiang, 315000
* Corresponding author.

Received date: 2022-09-05

  Revised date: 2022-10-17

  Online published: 2022-11-22

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摘要

芳香腈是有机合成中普遍存在的原料之一, 也是一类重要的合成中间体, 可广泛应用于药物、农用化学品、染料、香料以及功能材料等领域, 但由于C—CN键热力学稳定性较高, 很少被认为是一个有价值的反应位点. 因此, 开发简便、高效的方法催化芳香腈C—CN键转化成为近年研究热点之一. 综述了近十年来基于C—CN键断裂的芳香腈转化反应研究进展, 并按照不同反应原理分类, 主要包括过渡金属介导/催化的C—CN的转化、自由基介导的C—CN的转化、Lewis酸、碱或Brønsted酸介导的C—CN的转化, 详细讨论了反应底物普适性、反应机理和应用, 并对该领域的发展前景和局限性进行了总结.

关键词： 芳香腈; C—CN键断裂; 转化反应; 反应原理分类

本文引用格式

缪存静 , 姚佳琪 . 基于C—CN键断裂的芳香腈转化反应研究进展[J]. 有机化学, 2023 , 43(4) : 1341 -1364 . DOI: 10.6023/cjoc202209007

Abstract

Aromatic nitriles are one of the ubiquitous versatile materials in organic synthesis, and also a class of important synthetic intermediates for a wide range of applications in pharmaceuticals, agricultural chemicals, dyes, spices, and functional materials. However, the C—CN bond of aryl nitriles has rarely been considered as a valuable reaction site due to the high thermodynamic stability. Therefore, the development of simple and efficient methods to catalyze the C—CN bond transformation of aryl nitriles has become one of the hot research topics in recent years. In this review, the recent advances in the transformation reactions of aromatic nitriles via C—CN bond cleavage in the past decade are summarized and classified according to different reaction mechanisms, mainly including transition metal-mediated/catalyzed C—CN transformation, free radical-mediated C—CN transformation, Lewis acid, base or Brønsted acid-mediated C—CN transformation. The reaction substrate compatibility, mechanism, applications, advantages and limitations in this field are also discussed in detail.

Key words： aromatic nitriles; C—CN bond cleavage; transformation reaction; classification of reaction mechanisms

参考文献

[1]
Anbarasan, P.; Schareina, T.; Beller, M. Chem. Soc. Rev. 2011, 40, 5049.
[2]
(a) Trivedi, B. K.; Holmes, A.; Stoeber, T. L.; Blankley, C. J.; Roark, W. H.; Picard, J. A.; Shaw, M. K.; Essenburg, A. D.; Stanfield, R. L.; Krause, B. R. J. Med. Chem. 1993, 36, 3300.
[2]
(b) Weiberth, F. J.; Hall, S. S. J. Org. Chem. 1987, 52, 3901.
[2]
(c) Miller, J. S.; Manson, J. L. Acc. Chem. Res. 2001, 34, 563.
[3]
(a) Takagi, K.; Okamoto, T.; Sakakibara, Y.; Oka, S. Chem. Lett. 1973, 471.
[3]
(b) Zanon, J.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 2890.
[3]
(c) Sundermeier, M.; Zapf, A.; Beller, M. Eur. J. Inorg. Chem. 2003, 3513.
[3]
(d) Zhou, W.; Xu, J.; Zhang, L.; Jiao, N. Org. Lett. 2010, 12, 2888.
[4]
(a) So, Y.-H.; Miller, L. L. J. Am. Chem. Soc. 1980, 102, 7119.
[4]
(b) Dohi, T.; Morimoto, K.; Kiyono, Y.; Tohma, H.; Kita, Y. Org. Lett. 2005, 7, 537.
[4]
(c) Zhou, W.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 7094.
[4]
(d) Qin, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 15893.
[4]
(e) Pimparkar, S.; Koodan, A.; Maiti, S.; Ahmed, N. S.; Mostafa, M. M. M.; Maiti, D. Chem. Commun. 2021, 57, 2210.
[5]
(a) Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177.
[5]
(b) Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273.
[6]
Nakazawa, H.; Kamata, K.; Itazaki, M. Chem. Commun. 2005, 4004.
[7]
Nakazawa, H.; Itazaki, M.; Kamata, K.; Ueda, K. Chem. Asian J. 2007, 2, 882.
[8]
(a) Tobisu, M.; Nakamura, R.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 3174.
[8]
(b) Tobisu, M.; Nakamura, R.; Kita, Y.; Chatani, N. Bull. Korean Chem. Soc. 2010, 31, 582.
[9]
Patra, T.; Agasti, S.; Akanksha; Maiti, D. Chem. Commun. 2013, 49, 69.
[10]
Patra, T.; Agasti, S.; Modak, A.; Maiti, D. Chem. Commun. 2013, 49, 8362.
[11]
Weidauer, M.; Someya, C. I.; Irran, E.; Enthaler, S. Asian J. Org. Chem. 2013, 2, 150.
[12]
Enthaler, S.; Weidauer, M.; Irran, E.; Epping, J. D.; Kretschmer, R.; Someya, C. I. J. Organomet. Chem. 2013, 745-746, 262.
[13]
Hu?nig, S.; Schaller, R. Angew. Chem., Int. Ed. 1982, 21, 36.
[14]
(a) Nakao, Y. Chem. Rev. 2021, 121, 327.
[14]
(b) Wen, Q.; Lu, P.; Wang, Y. RSC Adv. 2014, 4, 47806.
[14]
(c) Kou, X.; Fan, J.; Tong, X.; Shen, Z. Chin. J. Org. Chem. 2013, 33, 1407. (in Chinese)
[14]
(寇学振, 范佳骏, 童晓峰, 沈增明, 有机化学, 2013, 33, 1407.)
[14]
(d) Paul, N.; Patra, T.; Maiti, D. Asian J. Org. Chem. 2022, 11, e202100591.
[15]
Sun, M.; Zhang, H. Y.; Han, Q.; Yang, K.; Yang, S. D. Chem. Eur. J. 2011, 17, 9566.
[16]
Liu, N.; Wang, Z.-X. Adv. Synth. Catal. 2012, 354, 1641.
[17]
Miller, J. A.; Dankwardt, J. W. Tetrahedron Lett. 2003, 44, 1907.
[18]
Yada, A.; Ebata, S.; Idei, H.; Zhang, D.; Nakao, Y.; Hiyama, T. Bull. Chem. Soc. Jpn 2010, 83, 1170.
[19]
(a) Nakao, Y.; Oda, S.; Hiyama, T. J. Am. Chem. Soc. 2004, 126, 13904.
[19]
(b) Nakao, Y.; Yukawa, T.; Hirata, Y.; Oda, S.; Satoh, J.; Hiyama, T. J. Am. Chem. Soc. 2006, 128, 7116.
[19]
(c) Nakao, Y.; Yada, A.; Ebata, S.; Hiyama, T. J. Am. Chem. Soc. 2007, 129, 2428.
[19]
(d) Ohnishi, Y.-Y.; Nakao, Y.; Sato, H.; Nakao, Y.; Hiyama, T.; Sakaki, S. Organometallics 2009, 28, 2583.
[20]
Nakai, K.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2011, 133, 11066.
[21]
Nakai, K.; Kurahashi, T.; Matsubara, S. Org. Lett. 2013, 15, 856.
[22]
Fang, X.; Yu, P.; Prina Cerai, G.; Morandi, B. Chem. Eur. J. 2016, 22, 15629.
[23]
Munjanja, L.; Torres-López, C.; Brennessel, W. W.; Jones, W. D. Organometallics 2016, 35, 2010.
[24]
Zhang, T.; Luan, Y. X.; Zheng, S. J.; Peng, Q.; Ye, M. Angew. Chem., Int. Ed. 2020, 59, 7439.
[25]
Wu, K.; Rong, Q.; Sun, N.; Hu, B.; Shen, Z.; Jin, L.; Hu, X. Adv. Synth. Catal. 2021, 363, 4708.
[26]
Delcaillau, T.; Morandi, B. Chem. Eur. J. 2021, 27, 11823.
[27]
Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
[28]
Kita, Y.; Tobisu, M.; Chatani, N. Org. Lett. 2010, 12, 1864.
[29]
(a) Chatani, N.; Tobisu, M.; Kinuta, H.; Kita, Y.; Rémond, E. Synthesis 2012, 44, 2999.
[29]
(b) Tobisu, M.; Kinuta, H.; Kita, Y.; Remond, E.; Chatani, N. J. Am. Chem. Soc. 2012, 134, 115.
[30]
Jiang, Y.-Y.; Yu, H.-Z.; Fu, Y. Organometallics 2013, 32, 926.
[31]
Esteruelas, M. A.; Oliván, M.; Vélez, A. J. Am. Chem. Soc. 2015, 137, 12321.
[32]
Wang, C.-S.; Yu, Y.; Sunada, Y.; Wang, C.; Yoshikai, N. ACS Catal. 2022, 12, 4054.
[33]
(a) McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114.
[33]
(b) Zuo, Z.; MacMillan, D. W. J. Am. Chem. Soc. 2014, 136, 5257.
[34]
(a) Dixon, I. M.; Collin, J.-P.; Sauvage, J.-P.; Flamigni, L.; Encinas, S.; Barigelletti, F. Chem. Soc. Rev. 2000, 29, 385.
[34]
(b) Mori, Y.; Sakaguchi, Y.; Hayashi, H. J. Phys. Chem. 2000, 104, 4896.
[35]
Panteleeva, E. V.; Vaganova, T. A.; Shteingarts, V. D.; Bilkis, I. I. Tetrahedron Lett. 1995, 36, 8465.
[36]
(a) Lewis, J. R. Nat. Prod. Rep. 2001, 18, 95.
[36]
(b) Lin, N.-H.; Carrera, G. M.; Anderson, D. J. J. Med. Chem. 1994, 37, 3542.
[37]
(a) Seel, S.; Thaler, T.; Takatsu, K.; Zhang, C.; Zipse, H.; Straub, B. F.; Mayer, P.; Knochel, P. J. Am. Chem. Soc. 2011, 133, 4774.
[37]
(b) Beng, T. K.; Gawley, R. E. Org. Lett. 2011, 13, 394.
[37]
(c) Campos, K. R.; Klapars, A.; Waldman, J. H.; Dormer, P. G.; Chen, C.-y. J. Am. Chem. Soc. 2006, 128, 3538.
[38]
Vega, J. A.; Alonso, J. M.; Mendez, G.; Ciordia, M.; Delgado, F.; Trabanco, A. A. Org. Lett. 2017, 19, 938.
[39]
Yan, C.; Li, L.; Liu, Y.; Wang, Q. Org. Lett. 2016, 18, 4686.
[40]
Ide, T.; Barham, J. P.; Fujita, M.; Kawato, Y.; Egami, H.; Hamashima, Y. Chem. Sci. 2018, 9, 8453.
[41]
Vorobév, A. Y. Chem. Heterocycl. Compd. 2019, 55, 90.
[42]
Campos, K.; Coleman, P.; Alvarez, J.; Dreher, S.; Garbaccio, R.; Terrett, N.; Tillyer, R.; Truppo, M.; Parmee, E. Science 2019, 363, eaat0805.
[43]
Nicastri, M. C.; Lehnherr, D.; Lam, Y. H.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2020, 142, 987.
[44]
Liu, Z.; Nan, X.; Lei, T.; Zhou, C.; Wang, Y.; Liu, W.; Chen, B.; Tung, C.; Wu, L. Chin. J. Catal. 2018, 39, 487.
[45]
Zhong, L. J.; Wang, H. Y.; Ouyang, X. H.; Li, J. H.; An, D. L. Chem. Commun. 2020, 56, 8671.
[46]
(a) Shahid, M.; Banakar, V. B.; Prabhakar Ganesh, P. S. K.; Gopinath, P. Asian J. Org. Chem. 2022, 11, e202200184.
[46]
(b) Ni, S.-F.; Huang, G.; Chen, Y.; Wright, J. S.; Li, M.; Dang, L. Coord. Chem. Rev. 2022, 455, 214255.
[46]
(c) Liu, B.; Romine, A. M.; Rubel, C. Z.; Engle, K. M.; Shi, B. F. Chem. Rev. 2021, 121, 14957.
[47]
Pirnot, M. T.; Rankic, D. A.; Martin, D. B. C.; MacMillan, D. W. C. Science 2013, 339, 1593.
[48]
Cuthbertson, J. D.; MacMillan, D. W. Nature 2015, 519, 74.
[49]
Chen, J.; Zhu, S.; Qin, J.; Chu, L. Chem. Commun. 2019, 55, 2336.
[50]
Hoshikawa, T.; Inoue, M. Chem. Sci. 2013, 4, 3118.
[51]
Lipp, B.; Nauth, A. M.; Opatz, T. J. Org. Chem. 2016, 81, 6875.
[52]
Nauth, A. M.; Lipp, A.; Lipp, B.; Opatz, T. Eur. J. Org. Chem. 2017, 2017, 2099.
[53]
Chen, Y.; Lu, P.; Wang, Y. Org. Lett. 2019, 21, 2130.
[54]
Shi, J.; Yuan, T.; Zheng, M.; Wang, X. ACS Catal. 2021, 11, 3040.
[55]
(a) Liu, B.; Lim, C.-H.; Miyake, G. M. J. Am. Chem. Soc. 2017, 139, 13616.
[55]
(b) Li, G.; Yan, Q.; Gan, Z.; Li, Q.; Dou, X.; Yang, D. Org. Lett. 2019, 21, 7938.
[56]
Kobayashi, F.; Fujita, M.; Ide, T.; Ito, Y.; Yamashita, K.; Egami, H.; Hamashima, Y. ACS Catal. 2020, 11, 82.
[57]
Lipp, B.; Lipp, A.; Detert, H.; Opatz, T. Org. Lett. 2017, 19, 2054.
[58]
Betori, R. C.; Scheidt, K. A. ACS Catal. 2019, 9, 10350.
[59]
Chen, D.; Xu, L.; Long, T.; Zhu, S.; Yang, J.; Chu, L. Chem. Sci. 2018, 9, 9012.
[60]
Wang, F.; Qin, J.; Zhu, S.; Chu, L. RSC Adv. 2020, 11, 142.
[61]
Yu, J. M.; Zhu, L. W.; Hong, X. Y.; Gao, H.; Chen, T. T. Org. Biomol. Chem. 2021, 19, 5642.
[62]
Ma, C.-H.; Ji, Y.; Zhao, J.; He, X.; Zhang, S.-T.; Jiang, Y.-Q.; Yu, B. Chin. J. Catal. 2022, 43, 571.
[63]
(a) Blakemore, D. C.; Castro, L.; Churcher, I.; Rees, D. C.; Thomas, A. W.; Wilson, D. M.; Wood, A. Nat. Chem. 2018, 10, 383.
[63]
(b) Liu, J.; Qiu, X.; Huang, X.; Luo, X.; Zhang, C.; Wei, J.; Pan, J.; Liang, Y.; Zhu, Y.; Qin, Q.; Song, S.; Jiao, N. Nat. Chem. 2019, 11, 71.
[64]
(a) Ruiz-Castillo, P.; Buchwald, S. L. Chem. Rev. 2016, 116, 12564.
[64]
(b) Chen, B.; Wu, L.-Z.; Tung, C.-H. Acc. Chem. Res. 2018, 51, 2512.
[65]
Miller, J. A.; Dankwardt, J. W.; Penney, J. M. Synthesis 2003, 1643.
[66]
Zhou, C.; Lei, T.; Wei, X. Z.; Ye, C.; Liu, Z.; Chen, B.; Tung, C. H.; Wu, L. Z. J. Am. Chem. Soc. 2020, 142, 16805.
[67]
Condon, S.; Dupré, D.; Lachaise, I.; Nédélec, J.-Y. Synthesis 2002, 1752.
[68]
(a) Xu, H.; Liu, J.; Nie, F.; Zhao, X.; Jiang, Z. J. Org. Chem. 2021, 86, 16204.
[68]
(b) Yang, J.; Ma, J.; Yan, K.; Tian, L.; Li, B.; Wen, J. Adv. Synth. Catal. 2021, 364, 845.
[68]
(c) Zhang, S.; Li, L.; Li, X.; Zhang, J.; Xu, K.; Li, G.; Findlater, M. Org. Lett. 2020, 22, 3570.
[68]
(d) Zhou, H. J.; Huang, J. M. J. Org. Chem. 2022, 87, 5328.
[69]
Zhang, X.; Yang, C.; Gao, H.; Wang, L.; Guo, L.; Xia, W. Org. Lett. 2021, 23, 3472.
[70]
Lehnherr, D.; Lam, Y. H.; Nicastri, M. C.; Liu, J.; Newman, J. A.; Regalado, E. L.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2020, 142, 468.
[71]
Wen, J.; Yang, X.; Yan, K.; Qin, H.; Ma, J.; Sun, X.; Yang, J.; Wang, H. Org. Lett. 2021, 23, 1081.
[72]
Thompson, A. D.; Huestis, M. P. J. Org. Chem. 2013, 78, 762.
[73]
Quinio, P.; Roman, D. S.; Leon, T.; William, S.; Karaghiosoff, K.; Knochel, P. Org. Lett. 2015, 17, 4396.
[74]
Chen, Q.; Leon, T.; Knochel, P. Angew. Chem., Int. Ed. 2014, 53, 8746.
[75]
(a) Li, M.; Gutierrez, O.; Berritt, S.; Pascual-Escudero, A.; Yesilcimen, A.; Yang, X.; Adrio, J.; Huang, G.; Nakamaru-Ogiso, E.; Kozlowski, M. C.; Walsh, P. J. Nat. Chem. 2017, 9, 997.
[75]
(b) Li, M.; Berritt, S.; Matuszewski, L.; Deng, G.; Pascual-Escudero, A.; Panetti, G. B.; Poznik, M.; Yang, X.; Chruma, J. J.; Walsh, P. J. J. Am. Chem. Soc. 2017, 139, 16327.
[75]
(c) Wang, Q.; Poznik, M.; Li, M.; Walsh, P. J.; Chruma, J. J. Adv. Synth. Catal. 2018, 360, 2854.
[76]
Zou, D.; Gan, L.; Yang, F.; Wang, H.; Pu, Y.; Li, J.; Walsh, P. J. Nat. Commun. 2021, 12, 7060.
[77]
Shelp, R. A.; Walsh, P. J. Angew. Chem. Int. Ed. 2018, 57, 15857.
[78]
Lei, Y.; Yang, J.; Qi, R.; Wang, S.; Wang, R.; Xu, Z. Chem. Commun. 2018, 54, 11881.
[79]
Takeda, M.; Nagao, K.; Ohmiya, H. Angew. Chem., Int. Ed. 2020, 59, 22460.
[80]
(a) Sato, Y.; Nakamura, K.; Sumida, Y.; Hashizume, D.; Hosoya, T.; Ohmiya, H. J. Am. Chem. Soc. 2020, 142, 9938;
[80]
(b) Buzzetti, L.; Prieto, A.; Roy, S. R.; Melchiorre, P. Angew. Chem., Int. Ed. 2017, 56, 15039.
[81]
Reidl, T. W.; Bandar, J. S. J. Am. Chem. Soc. 2021, 143, 11939.
[82]
Gao, L.; Wang, G.; Cao, J.; Chen, H.; Gu, Y.; Liu, X.; Cheng, X.; Ma, J.; Li, S. ACS Catal. 2019, 9, 10142.
[83]
Wang, G.; Cao, J.; Gao, L.; Chen, W.; Huang, W.; Cheng, X.; Li, S. J. Am. Chem. Soc. 2017, 139, 3904.
[84]
Tang, L.; Jiang, S.; Huang, X.; Song, Z.; Wang, J. B.; Ma, M.; Chen, B.; Ma, Y. Org. Lett. 2022, 24, 3232.
[85]
Cao, J.; Wang, G.; Gao, L.; Chen, H.; Liu, X.; Cheng, X.; Li, S. Chem. Sci. 2019, 10, 2767.
[86]
Gao, L.; Liu, X.; Li, G.; Chen, S.; Cao, J.; Wang, G.; Li, S. Org. Lett. 2022, 24, 5698.
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