Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (7): 2063-2076.DOI: 10.6023/cjoc202403017 Previous Articles Next Articles
REVIEWS
收稿日期:
2024-03-12
修回日期:
2024-04-13
发布日期:
2024-04-24
基金资助:
Qian Chena,b, Zhaobin Hanb(), Kuiling Dingb,c,d()
Received:
2024-03-12
Revised:
2024-04-13
Published:
2024-04-24
Contact:
E-mail: Supported by:
Share
Qian Chen, Zhaobin Han, Kuiling Ding. Transition Metal Catalyzed Carbocycle-Selective Asymmetric Hydrogenation of Aromatic Rings[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2063-2076.
[1] |
(a) Wertjes, W. C.; Southgate, E. H.; Sarlah, D. Chem Soc. Rev. 2018, 47, 7996.
|
(b) Roche, S. P.; Porco, Jr., J. A. Angew. Chem., Int. Ed. 2011, 50, 4068.
|
|
[2] |
(a) Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557.
|
(b) Zhang, Z.; Butt, N. A.; Zhang, W. Chem. Rev. 2016, 116, 14769.
|
|
(c) Kim, A. N.; Stoltz, B. M. ACS Catal. 2020, 10, 13834.
|
|
(d) Gunasekar, R.; Goodyear, R. L.; Silvestri, I. P.; Xiao, J. Org. Biomol. Chem. 2022, 20, 1794.
|
|
(e) Lu, S.-M.; Han, X.-W.; Zhou, Y.-G. Chin. J. Org. Chem. 2005, 25, 634. (in Chinese)
|
|
(卢胜梅, 韩秀文, 周永贵, 有机化学, 2005, 25, 634.)
|
|
[3] |
(a) Wiesenfeldt, M. P.; Nairoukh, Z.; Dalton, T.; Glorius, F. Angew. Chem., Int. Ed. 2019, 58, 10460.
doi: 10.1002/anie.201814471 pmid: 37427715 |
(b) Lückemeier, L.; Pierau, M.; Glorius, F. Chem. Soc. Rev. 2023, 52, 4996.
doi: 10.1039/d3cs00329a pmid: 37427715 |
|
[4] |
Ding, K.; Uozumi, Y. Handbook of Asymmetric Heterogeneous Catalysis, Wiley, Weinheim, 2008.
|
(b) Nishimura, S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley, New York, 2001.
|
|
[5] |
Meemken, F.; Baiker, A. Chem. Rev. 2017, 117, 11522.
doi: 10.1021/acs.chemrev.7b00272 pmid: 28872309 |
[6] |
Nasar, K.; Fache, F.; Lemaire, M.; Béziat, J.-C.; Besson, M.; Gallezot, P. J. Mol. Catal. 1994, 87, 107.
|
[7] |
Jansat, S.; Picurelli, D.; Pelzer, K.; Philippot, K.; Gómez, M.; Muller, G.; Lecante, P.; Chaudret, B. New J. Chem. 2006, 30, 115.
|
[8] |
(a) Gual, A.; Axet, M. R.; Godard, C.; Philippot, K.; Chaudret, B.; Denicourt-Nowicki, A.; Roucoux, A.; Castillon, S.; Claver, C. Chem. Commun. 2008, 2759.
|
(b) Gual, A.; Godard, C.; Philippot, K.; Chaudret, B.; Denicourt-Nowicki, A.; Roucoux, A.; Castillon, S.; Claver, C. ChemSusChem 2009, 2, 769.
|
|
[9] |
(a) Landré, P. D.; Lemaire, M.; Richard, D.; Gallezot, P. J. Catal. 1994, 147, 214.
|
(b) Besson, M.; Gallezot, P.; Neto, S.; Pinel, C. Chem. Commun. 1998, 1431.
|
|
(c) Ranade, V. S.; Prins, R. J. Catal. 1999, 185, 479.
|
|
(d) Ranade, V. S.; Consiglio, G.; Prins, R. Catal. Lett. 1999, 58, 71.
|
|
(e) Barbosa, L. A. M. M.; and Sautet, P. J. Catal. 2003, 217, 23.
|
|
[10] |
Heitbaum, M.; Frçhlich, R.; Glorius, F. Adv. Synth. Catal. 2010, 352, 357.
|
[11] |
(a) Ranade, V. S.; Consiglio, G.; Prins, R. J. Org. Chem. 1999, 64, 8862.
pmid: 10814064 |
(b) Ranade, V. S.; Consiglio, G.; Prins, R. J. Org. Chem. 2000, 65, 1132.
pmid: 10814064 |
|
[12] |
(a) Sayago, F. J.; Calaza, M. I.; Jiménez, A. I.; Cativiela, C. Tetrahedron 2008, 64, 84.
|
(b) Vincent, M.; Remond, G.; Portevin, B.; Serkiz, B.; Laubie, M. Tetrahedron Lett. 1982, 23, 1677.
|
|
[13] |
Gohring, W.; Gokhale, S.; Hilpert, H.; Roessler, F.; Schlageter, M.; Vogt, M. Chimia 1996, 50, 532.
|
[14] |
Wei, Y.; Rao, B.; Cong, X.-F.; Zeng, X.-M. J. Am. Chem. Soc. 2015, 137, 9250.
doi: 10.1021/jacs.5b05868 pmid: 26172049 |
[15] |
Tran, B. L.; Fulton, J. L.; Linehan, J. C.; Lercher, J. A.; Bullock, R. M. ACS Catal. 2018, 8, 8441.
|
[16] |
(a) Wiesenfeldt, M. P.; Nairoukh, Z.; Li, W.; Glorius, F. Science 2017, 357, 908.
doi: 10.1126/science.aao0270 pmid: 30394616 |
(b) Wiesenfeldt, M. P.; Knecht, T.; Schlepphorst, C.; Glorius, F. Angew. Chem., Int. Ed. 2018, 57, 8297.
doi: 10.1002/anie.201804124 pmid: 30394616 |
|
(c) Wollenburg, M.; Moock, D.; Glorius, F. Angew. Chem., Int. Ed. 2019, 58, 6549.
doi: 10.1002/anie.201810714 pmid: 30394616 |
|
[17] |
Ling, L.; He, Y.; Zhang, X.; Luo, M.-M. Zeng, X.-M. Angew. Chem., Int. Ed. 2019, 58, 6554.
|
[18] |
(a) Schiwek, C. H.; Jandl, C.; Bach, T. Org. Lett. 2020, 22, 9468.
|
(b) Schiwek, C. H.; Jandl, C.; Bach, T. ACS Catal. 2022, 12, 3628.
|
|
[19] |
Muetterties, E. L.; Hirsekorn, F. J. J. Am. Chem. Soc. 1974, 96, 4063.
|
[20] |
Johnson, J. W.; Muetterties, E. L. J. Am. Chem. Soc. 1977, 99, 7395.
|
[21] |
Boxwell, C. J.; Dyson, P. J.; Ellis, D. J.; Welton, T. J. Am. Chem. Soc. 2002, 124, 9334.
pmid: 12167003 |
[22] |
Borowski, A. F.; Sabo-Etienne, S.; Donnadieu, B.; Chaudret, B. Organometallics 2003, 22, 1630.
|
[23] |
Klabunde, K. J.; Anderson, B. B.; Bader, M.; Radonovich, L. J. J. Am. Chem. Soc. 1978, 100, 1313.
|
[24] |
Pieta, D.; Trzeciak, A. M.; Ziółkowski, J. J. J. Mol. Catal. 1983, 18, 193.
|
[25] |
Yu, J. S.; Rothwell, I. P. J. Chem. Soc., Chem. Commun. 1992, 632.
|
[26] |
Urban, S.; Ortega, N.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 3803.
|
[27] |
Paul, D.; Beiring, B.; Plois, M.; Ortega, N.; Kock, S.; Schlüns, D.; Neugebauer, J.; Wolf, R.; Glorius, F. Organometalics 2016, 35, 3641.
|
[28] |
Kuwano, R.; Morioka, R.; Kashiwabara, M.; Kameyama, N. Angew. Chem., Int. Ed. 2012, 51, 4136.
|
[29] |
Kuwano, R.; Ikedaa, R.; Hirasada, K. Chem. Commun. 2015, 51, 7558.
|
[30] |
Jin, Y.; Makida, Y.; Uchida, T.; Kuwano, R. J. Org. Chem. 2018, 83, 3829.
|
[31] |
Yan, Z.; Xie, H.-P.; Shen, H.-Q.; Zhou, Y.-G. Org. Lett. 2018, 20, 1094.
|
[32] |
(a) Luo, Y.-E.; He, Y.-M.; Fan, Q.-H. Chem. Rec. 2016, 16, 2697.
|
(b) Li, C.-H.; Zhang, S.-X.; Feng, Y.; He, Y.-M.; Fan, Q.-H. Chin. J. Chem. 2023, 41, 3573.
|
|
[33] |
Zhang, S.-X.; Xu, C.; Yi, N.-N.; Li, S.; He, Y.-M.; Feng, Y.; Fan, Q.-H. Angew. Chem., Int. Ed. 2022, 61, e202205739.
|
[34] |
Touge, T.; Sakaguchi, K.; Tamaki, N.; Nara, H.; Yokozawa, T.; Matsumura, K.; Kayaki, Y. J. Am. Chem. Soc. 2019, 141, 16354.
|
[35] |
(a) de Vries, J. G.; Elsevier, C. J. Handbook of Homogeneous Hydrogenation, Vol. 1-3, Wiley, Weinheim, 2010.
|
(b) Nie, Y.; Li, J.; Yuan, Q.; Zhang, W. Chin. J. Chem. 2022, 40, 819.
|
|
[36] |
Ding, Y.-X.; Zhu, Z.-H.; Chen, M.-W.; Yu, C.-B.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2022, 61, e202205623.
|
[37] |
(a) Chirik, P.; Morris, R. Acc. Chem. Res. 2015, 48, 2495.
|
(b) Liu, C.; Liu, Q. Chin. J. Org. Chem. 2020, 40, 3963. (in Chinese)
|
|
(刘晨光, 刘强, 有机化学, 2020, 40, 3963.)
|
|
(c) Wu, L.; Wei, H.; Shen, J.; Chen, J.; Zhang, W. Acta Chim. Sinica 2021, 79, 1331. (in Chinese)
|
|
(吴良, 魏瀚林, 申杰峰, 陈建中, 张万斌, 化学学报, 2021, 79, 1331.)
doi: 10.6023/A21070338 |
|
(d) Cai, X.; Chen, J.; Zhang. W. Acta Chim. Sinica 2023, 81, 646. (in Chinese)
|
|
(蔡新红, 陈建中, 张万斌, 化学学报, 2023, 81, 646.)
doi: 10.6023/A23040140 |
|
[38] |
Viereck, P.; Hierlmeier, G.; Tosatti, P.; Pabst, T. P.; Puentener, K.; Chirik, P. J. J. Am. Chem. Soc. 2022, 144, 11203.
doi: 10.1021/jacs.2c02007 pmid: 35714999 |
[39] |
(a) Liang, Q.-J.; Xu, Y.-H.; Loh, T.-P. Org. Chem. Front. 2018, 5, 2765.
|
(b) Zhou, J. Chem.-Asian J. 2010, 5, 422.
|
|
[40] |
Moock, D.; Wagener, T.; Hu, T.; Gallagher, T.; Glorius, F. Angew. Chem., Int. Ed. 2021, 60, 13677.
|
[41] |
Ortega, N.; Urban, S.; Beiring, B.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 1710.
doi: 10.1002/anie.201107811 pmid: 22311814 |
[42] |
Wu, H.-B.; Yang, J.-P.; Peters, B. B. C.; Massaro, L.; Zheng, J.; Andersson, P. G. J. Am. Chem. Soc. 2021, 143, 20377.
|
[43] |
Zhang, F.; Sasmal, H. S.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2023, 145, 15695.
|
[44] |
(a) Zhong, J.; Chen, J.; Chen, L. Catal. Sci. Technol. 2014, 4, 3555.
|
(b) Li, H.; Wang, Y.; Lai, Z.; Huang, K.-W. ACS Catal. 2017, 7, 4446.
|
|
[45] |
Li, X.-L.; Hao, W.; Yi, N.-N.; He, Y.-M.; Fan, Q.-H. CCS Chem. 2023, 5, 2277.
|
[1] | Yongsheng Tian, Lanfeng Wei, Jiawei Huang, Yu Wei, Liang Xu, Shuai Liu. Deboronative Selenylation, Bromination, or Hydroxylation of Organic Boronic Acids Facilitated by Tetrabutylammonium Tribromide under Transition Metal-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1987-1997. |
[2] | Guangli Xu, Hongping Han, Luwei Cao, Simin Hong, linyue Hai, Xiang Cui. Research Progress of Transition Metal-Catalyzed Synthesis of 1,3-Conjugated Dienyl Boron Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1480-1493. |
[3] | Kaijie Guo, Xinshu Fu, Jing Li, Yan Chen, Meili Hu, Xihua Du, Yuyang Xie, Yan He. Recent Advances in Transition-Metal-Catalyzed C—S Bond Activation and Transformations [J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1124-1150. |
[4] | Tianfeng Peng, Yuxiang Zhao, Shaojian Pu, Juan Luo, Teng Liu, Yingchun Miao, Xianfu Shen. Recent Advances in Total Synthesis of Prenylated Indole Alkaloids by Transition Metal-Catalyzed Reactions as the Key Step [J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1160-1180. |
[5] | Chen-Long Li, Zhi-Xiang Yu. Progress in Transition-Metal-Catalyzed Carbonylative Cycloadditions Using Carbon Monoxide [J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1045-1068. |
[6] | Jie Liu, Feng Han, Shuangyan Li, Tianyu Chen, Jianhui Chen, Qing Xu. Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 573-583. |
[7] | Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84. |
[8] | Jing Tang, Wenkun Luo, Jun Zhou. Advances in the Synthesis of Azaspiro[4.5]trienones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3006-3034. |
[9] | Wenfang Wang. Recent Progress in Transition-Metal-Catalyzed Asymmetric C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3146-3166. |
[10] | Xiaoyang Gao, Ruirui Zhai, Xun Chen, Shuojin Wang. Recent Progress in C—H Bond Activation Reaction with Vinylene Carbonate [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3119-3134. |
[11] | Zhongrong Xu, Jieping Wan, Yunyun Liu. Transition Metal-Free C—H Thiocyanation and Selenocyanation Based on Thermochemical, Photocatalytic and Electrochemical Process [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2425-2446. |
[12] | Sifan Dong, Haolong Li, Yuan Qin, Shiming Fan, Shouxin Liu. Research Progress of Amino Acids as Transient Directing Groups in C—H Bond Activation Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2351-2367. |
[13] | Yangyang Chu, Zhaobin Han, Kuiling Ding. Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1934-1951. |
[14] | Xiaojing Hu, Feixiang Guo, Runqing Zhu, Bingqi Zhou, Tao Zhang, Lizhen Fang. Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2239-2244. |
[15] | Jiao Qin, Jie Chen, Yan Su. Synthesis of 2,2,6,6-Tetramethylpiperidin-1-yl-2-(2-cyanophenyl)-acetate by Transition Metal-Free Radical Cleavage Reaction from α-Bromoindanone [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2171-2177. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||