过渡金属催化芳香碳环的选择性不对称氢化

doi:10.6023/cjoc202403017

摘要/Abstract

(杂)芳烃中碳环的不对称氢化是制备饱和以及部分饱和手性六元碳环化合物最直接高效的方法之一. 尽管(杂)芳烃的不对称氢化在反应活性、选择性等方面存在着很大的挑战, 但近年来该领域还是取得了一些突破. 系统地综述了过去几十年过渡金属催化的芳烃中碳环不对称氢化的研究进展, 并讨论了该领域存在的问题及可能的发展方向.

关键词: 过渡金属, (杂)芳烃, 不对称氢化, 去芳构化

Asymmetric hydrogenation of carbon rings in (hetero)arenes is one of the most direct and efficient methods for preparing saturated and partially saturated chiral six membered carbon ring compounds. While significant challenges in terms of low reactivity and selectivity remain, some breakthroughs have been made in this field of carbocycle-selective asymmetric hydrogenation of (hetero)arenes in recent years. The research progress of transition metal catalyzed carbocycle-selective asymmetric hydrogenation of (hetero)arenes in the past few decades is summarized, and the prospects of further developments are also discussed.

Key words: transition metal, (hetero)arene, asymmetric hydrogenation, dearomatization

引用此文

陈倩, 韩召斌, 丁奎岭. 过渡金属催化芳香碳环的选择性不对称氢化[J]. 有机化学, 2024, 44(7): 2063-2076.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 16

图式1. 邻二取代苯不对称氢化中的化学、非对映和对映选择性

Scheme 1. Chemo-, diastereo- and enantioselectivities in the asymmetric hydrogenation of ortho-substituted benzenes

图式2. 异相催化的手性辅基诱导的(杂)芳烃的非对映选择性氢化

Scheme 2. Heterogeneous catalytic diastereoselective hydrogenation of (hetero)arenes induced by chiral auxiliaries

图式3. 异相催化的手性底物诱导的芳烃的非对映选择性氢化

Scheme 3. Heterogeneous catalytic diastereoselective hydrogenation of arenes induced by chiral substrate

图式4. 铑络合物17~19催化的手性底物诱导的芳烃的非对映选择性氢化

Scheme 4. Rh complexes 17~19 catalyzed diastereoselective hydrogenation of arenes induced by chiral substrates

图式5. 碳环选择性的(杂)芳烃的均相催化氢化

Scheme 5. Homogeneous catalytic hydrogenation of (hetero)- arenes with carbocycle selectivity

图式6. 钌/SINpEt催化的取代喹喔啉的不对称氢化

Scheme 6. Ru/SINpEt catalyzed asymmetric hydrogenation of substituted quinoxalines

图式7. 钌/PhTrap催化的取代萘的不对称氢化

Scheme 7. Ru/PhTrap catalyzed asymmetric hydrogenation of substituted naphthalenes

图式8. 钌/PhTrap催化的取代喹啉和异喹啉的不对称氢化

Scheme 8. Ru/PhTrap catalyzed asymmetric hydrogenation of substituted quinolones and isoquinolines

图式9. 钌催化的N-(9-菲基)乙酰胺的不对称氢化

Scheme 9. Ru-catalyzed asymmetric hydrogenation of N-(phenanthren-9-yl)acetamides

图式10. 钌催化的9-菲酚的不对称氢化

Scheme 10. Ru-catalyzed asymmetric hydrogenation of 9-phenanthrols

图式11. 铑催化的取代蒽、萘和菲的不对称氢化

Scheme 11. Rh-catalyzed asymmetric hydrogenation of substituted anthracenes, naphthalenes and phenanthrenes

图式12. 钼催化的取代喹啉和萘的不对称氢化

Scheme 12. Mo-catalyzed asymmetric hydrogenation of substituted quinolones and naphthalenes

图式13. 苯并呋喃和2,6-二甲基萘的接力催化不对称完全氢化

Scheme 13. Complete asymmetric hydrogenation of benzofurans and 2,6-dimethylnaphthalene by relay catalysis

图式14. 均相手性铑/异相铑接力催化取代芳基乙烯的不对称完全氢化

Scheme 14. Complete asymmetric hydrogenation of substituted vinylarenes with homogeneous chiral rhodium complex and heterogeneous rhodium relay catalysis

图式15. 双功能手性钌络合物催化的取代吲哚和苯并呋喃的不对称完全氢化反应

Scheme 15. Complete asymmetric hydrogenation of substituted indoles and benzofurans using chiral ruthenium complex with dual function

图式16. 协同异相-均相催化的取代萘酚和苯酚的不对称转移氢化

Scheme 16. Asymmetric transfer hydrogenation of substituted naphthols and phenols with cooperative heterogeneous and homogeneous catalysis

参考文献 45

[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.