综述与进展

铱催化的(杂)芳烃远端区域选择性C—H硼化反应的最新进展

  • 邹晓亮 ,
  • 徐森苗
展开
  • a 中国科学院兰州化学物理研究所 羰基合成与选择氧化国家重点实验室 兰州 730000
    b 中国科学院大学 北京 100049

收稿日期: 2021-03-10

  修回日期: 2021-03-17

  网络出版日期: 2021-03-25

基金资助

国家自然科学基金(91956116)

Recent Progress in Iridium-Catalyzed Remote Regioselective C—H Borylation of (Hetero)Arenes

  • Xiaoliang Zou ,
  • Senmiao Xu
Expand
  • a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
    b University of Chinese Academy of Sciences, Beijing 100049
* Corresponding author. E-mail:

Received date: 2021-03-10

  Revised date: 2021-03-17

  Online published: 2021-03-25

Supported by

National Natural Science Foundation of China(91956116)

摘要

(杂)芳基硼酸及其衍生物在合成化学、材料科学和药物化学领域具有广泛的用途, 因此, 其合成方法研究一直备受关注. 铱催化的C—H硼化反应是合成这类化合物最为有效的途径之一, 然而, 由于反应机理的限制, 区域选择性可控的C—H硼化是铱催化体系的一大挑战, 同时也是该领域的一个重要发展方向. 系统介绍了最近几年铱催化的芳烃远端硼氢化反应的最新进展.

本文引用格式

邹晓亮 , 徐森苗 . 铱催化的(杂)芳烃远端区域选择性C—H硼化反应的最新进展[J]. 有机化学, 2021 , 41(7) : 2610 -2620 . DOI: 10.6023/cjoc202103020

Abstract

(Hetero)Aryl boronic acids and their derivatives have been widely used in synthetic chemistry, material sciences, and drug discovery. Accordingly, the development of novel synthetic methods towards these structures has received a great deal of attention. In particular, Ir-catalyzed C—H borylation represents one of the most efficient methods. Due to the restriction of the reaction mechanism, regioselective controllable C—H borylation of Ir catalysis is a formidable challenge, and it is also an important development direction in this area. In this review, the recent progress in Ir-catalyzed remote selective C—H borylation of arenes is systematically discussed.

参考文献

[1]
Mkhalid,I. A.I.; Barnard,J. H.; Marder,T. B.; Murphy,J. M.; Hartwig,J. F. Chem. Rev. 2010, 110,890.
[2]
Zhu,D. -X.; Xu,M. -H. Chin. J. Org. Chem. 2020, 40,255 (in Chinese).
[2]
( 祝东星, 徐明华, 有机化学, 2020, 40,255.)
[3]
Liu, W.; Lu, Z. Chin. J. Org. Chem. 2020, 40,3596 (in Chinese).
[3]
( 刘文伯, 陆展, 有机化学, 2020, 40,3596.)
[4]
Xu, H.; Jiang, Z. Chin. J. Org. Chem. 2020, 40,3483 (in Chinese).
[4]
( 许荷欢, 江智勇, 有机化学, 2020, 40,3483.)
[5]
Yang,J. -M.; Li,Z. -Q.; Zhu,S. -F. Chin. J. Org. Chem. 2017, 37,2481 (in Chinese).
[5]
( 杨吉民, 李子奇, 朱守非, 有机化学, 2017, 37,2481.)
[6]
Jiang,Z. -T.; Wang, Bi-Q.; Shi,Z. -J. Chin. J. Chem. 2018, 36,950.
[7]
Zhan, M.; Song, P.; Jiao, J.; Li, P. Chin. J. Chem. 2020, 38,665.
[8]
Wang,Y. -X.; Zhang,P. -F.; Ye, M. Chin. J. Chem. 2020, 38,1762.
[9]
Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi,N. R.; Hartwig,J. F. J. Am. Chem. Soc. 2002, 124,390.
[10]
Cho,J. -Y.; Tse,M. K.; Holmes, D.; Maleczka,R. E.; Smith,M. R. Science 2002, 295,305.
[11]
Boller,T. M.; Murphy,J. M.; Hapke, M.; Ishiyama, T.; Miyaura, N.; Hartwig,J. F. J. Am. Chem. Soc. 2005, 127,14263.
[12]
Boebel,T. A.; Hartwig,J. F. J. Am. Chem. Soc. 2008, 130,7534.
[13]
Robbins,D. W.; Boebel,T. A.; Hartwig,J. F. J. Am. Chem. Soc. 2010, 132,4068.
[14]
Preshlock,S. M.; Plattner,D. L.; Maligres,P. E.; Krska,S. W.; Maleczka,R. E.; Smith,M. R. Angew. Chem.,Int. Ed. 2013, 52,12915.
[15]
Roosen,P. C.; Kallepalli,V. A.; Chattopadhyay, B.; Singleton,D. A.; Maleczka,R. E.; Smith,M. R. J. Am. Chem. Soc. 2012, 134,11350.
[16]
Li,H. -L.; Kanai, M.; Kuninobu, Y. Org. Lett. 2017, 19,5944.
[17]
Liang,L. H.; Yoichiro, K.; Motomu, K. Angew. Chem.,Int. Ed. 2017, 56,1495.
[18]
Ishiyama, T.; Isou, H.; Kikuchi, T.; Miyaura, N. Chem. Commun. 2010, 46,159.
[19]
Sasaki, I.; Taguchi, J.; Hiraki, S.; Ito, H.; Ishiyama, T. Chem.-Eur. J. 2015, 21,9236.
[20]
Kawamorita, S.; Ohmiya, H.; Hara, K.; Fukuoka, A.; Sawamura, M. J. Am. Chem. Soc. 2009, 131,5058.
[21]
Kawamorita, S.; Ohmiya, H.; Sawamura, M. J. Org. Chem. 2010, 75,3855.
[22]
Yamazaki, K.; Kawamorita, S.; Ohmiya, H.; Sawamura, M. Org. Lett. 2010, 12,3978.
[23]
Crawford,K. M.; Ramseyer,T. R.; Daley,C. J.A.; Clark,T. B. Angew. Chem.,Int. Ed. 2014, 53,7589.
[24]
Roering,A. J.; Hale,L. V.A.; Squier,P. A.; Ringgold,M. A.; Wiederspan,E. R.; Clark,T. B. Org. Lett. 2012, 14,3558.
[25]
Hale,L. V.A.; McGarry,K. A.; Ringgold,M. A.; Clark,T. B. Organometallics 2015, 34,51.
[26]
Ros, A.; Estepa, B.; López-Rodríguez, R.; Álvarez, E.; Fernández, R.; Lassaletta,J. M. Angew. Chem.,Int. Ed. 2011, 50,11724.
[27]
Ros, A.; López-Rodríguez, R.; Estepa, B.; Álvarez, E.; Fernández, R.; Lassaletta,J. M. J. Am. Chem. Soc. 2012, 134,4573.
[28]
Ghaffari, B.; Preshlock,S. M.; Plattner,D. L.; Staples,R. J.; Maligres,P. E.; Krska,S. W.; Maleczka,R. E.; Smith,M. R. J. Am. Chem. Soc. 2014, 136,14345.
[29]
Wang, G.; Liu, L.; Wang, H.; Ding,Y. -S.; Zhou, J.; Mao, S.; Li, P. J. Am. Chem. Soc. 2017, 13,91.
[30]
Ros, A.; Fernandez, R.; Lassaletta,J. M. Chem. Soc. Rev. 2014,43 3229.
[31]
Hartwig,J. F. Chem. Soc. Rev. 2011, 40,1992.
[32]
Xu, L.; Wang, G.; Zhang, S.; Wang, H.; Wang, L.; Liu, L.; Jiao, J.; Li, P. Tetrahedron 2017, 73,7123.
[33]
Feng, Y.; Holte, D.; Zoller, J.; Umemiya, S.; Simke,L. P.; Baran,P. S. J. Am. Chem. Soc. 2015, 137,10160.
[34]
Kuninobu, Y.; Ida, H.; Nishi, M.; Kanai, M. Nat. Chem. 2015, 7,712.
[35]
Lu, X.; Yoshigoe, Y.; Ida, H.; Nishi, M.; Kanai, M.; Kuninobu, Y. ACS Catal. 2019, 9,1705.
[36]
Bisht, R.; Chattopadhyay, B. J. Am. Chem. Soc. 2016, 138,84.
[37]
Hoque,M. E.; Bisht, R.; Haldar, C.; Chattopadhyay, B. J. Am. Chem. Soc. 2017, 139,7745.
[38]
Davis,H. J.; Mihai,M. T.; Phipps,R. J. J. Am. Chem. Soc. 2016, 138,12759.
[39]
Mihai,M. T.; Davis,H. J.; Genov,G. R.; Phipps,R. J. ACS Catal. 2018, 8,3764.
[40]
Lee, B.; Mihai,M. T.; Stojalnikova, V.; Phipps,R. J. J. Org. Chem. 2019, 84,13124.
[41]
Davis,H. J.; Genov,G. R.; Phipps,R. J. Angew. Chem.,Int. Ed. 2017, 56, 13351.
[42]
Genov,G. R.; Douthwaite,J. L.; Lahdenperä,A. S.K.; Gibson,D. C.; Phipps,R. J. Science 2020, 367,1246.
[43]
Mihai,M. T.; Williams,B. D.; Phipps,R. J. J. Am. Chem. Soc. 2019, 141,15477.
[44]
Saito, Y.; Segawa, Y.; Itami, K. J. Am. Chem. Soc. 2015, 137,5193.
[45]
Okumura, S.; Tang, S.; Saito, T.; Semba, K.; Sakaki, S.; Nakao, Y. J. Am. Chem. Soc. 2016, 138,14699.
[46]
Yang, L.; Semba, K.; Nakao, Y. Angew. Chem.,Int. Ed. 2017, 56,4853.
[47]
Yang, L.; Uemura, N.; Nakao, Y. J. Am. Chem. Soc. 2019, 141,7972.
[48]
Trouvé, J.; Zardi, P.; Al-Shehimy, S.; Roisnel, T.; Gramage-Doria, R. Angew. Chem.,Int. Ed. 10.1002/anie.202101997.
文章导航

/