Applications of Phosphoramidite Ligands in Ir-Catalyzed Asymmetric Hydrogenation Reactions

doi:10.6023/cjoc201509016

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (2): 274-282.DOI: 10.6023/cjoc201509016 Previous Articles Next Articles

Reviews

亚磷酰胺配体在铱催化不对称氢化反应中的应用 2017-2018 Awarded

袁乾家, 张万斌

上海交通大学化学化工学院上海 200240

收稿日期:2015-09-13 修回日期:2015-10-13 发布日期:2015-10-23
通讯作者: 张万斌 E-mail:wanbin@sjtu.edu.cn
基金资助:
国家自然科学基金(No. 21232004)和上海市优秀学科带头人(No. 14XD1402300)资助项目.

Applications of Phosphoramidite Ligands in Ir-Catalyzed Asymmetric Hydrogenation Reactions

Yuan Qianjia, Zhang Wanbin

School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received:2015-09-13 Revised:2015-10-13 Published:2015-10-23
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21232004), and the Program of Shanghai Subject Chief Scientists (No. 14XD1402300).

Phosphoramidites, as a class of privileged chiral ligands, are suitable for different types of reactions, such as catalytic asymmetric hydrogenation, catalytic asymmetric allylic substitution, catalytic asymmetric Diels-Alder reaction and so on. Catalytic asymmetric hydrogenation reactions are some of the most important reactions in industry. In this review recent advances and applications of phosphoramidite ligands in Ir-catalyzed asymmetric hydrogenation of enamides and their derivatives, unfunctionalized enamines, imines and heteroaromatic compounds are discussed.

Key words: phosphoramidites, iridium, catalytic asymmetric hydrogenation

Cite this article

Yuan Qianjia, Zhang Wanbin. Applications of Phosphoramidite Ligands in Ir-Catalyzed Asymmetric Hydrogenation Reactions[J]. Chin. J. Org. Chem., 2016, 36(2): 274-282.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008. (b) 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.) (c) de Vries, J. G.; Elsevier, C. J. Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim, 2007. (d) Ma, Y.-H.; Zhang, Y.-J.; Zhang, W. Chin. J. Org. Chem. 2007, 27, 289 (in Chinese). (马元辉, 张勇健, 张万斌, 有机化学, 2007, 27, 289.) (e) Blaser, H. U.; Federsel. H.-J. Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions, 2nd ed., Wiley-VCH, Weinheim, 2010. (f) Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713.
[2] (a) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921. (b) Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258. (c) Zhang, W.; Liu, D. In Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications, Chapter 7, Wiley-VCH, Weinheim, 2010. (d) Kazmaier, U. Transition Meatl Catalyzed Enantioselective Allylic Substitution in Organic Synthesis, Springer: New York, 2012. (e) Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558.
[3] (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007. (b) Kobayashi, S.; Jorgenson, K. A. Cycloaddition Reaction in Organic Synthesis, New York, Wiley-VCH, 2002. (c) Desimoni, G.; Faita, G.; Jorgenson, K. A. Chem. Rev. 2006, 106, 3561.
[4] (a) Porter, M. J.; Skidmore, J. Chem. Commun. 2000, 36, 1215. (b) Xia, Q.-H.; Ge, H.-Q.; Ye, C.-P.; Liu, Z.-M.; Su, K.-X. Chem. Rev. 2005, 105, 1603.
[5] (a) RajanBabu, T. V. Chem. Rev. 2003, 103, 2845. (b) Jia, X.; Wang, Z.; Xia, C.; Ding, K. C. Chin. J. Org. Chem. 2013, 33, 1369 (in Chinese) (贾肖飞, 王正, 夏春谷, 丁奎岭, 有机化学, 2013, 33, 1369.)
[6] (a) Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691. (b) Teichert, J. F.; Feringa, B. L. Angew. Chem., Int. Ed. 2010, 49, 2486. (c) Zhang, Z.; Xie, F.; Yang, B.; Yu, H.; Zhang, W. Chin. J. Org. Chem. 2011, 31, 429 (in Chinese). (张振锋, 谢芳, 杨波, 余焓, 张万斌, 有机化学, 2011, 31, 429.) (d) Zhou, Q.-L. Privileged Chiral Ligands and Catalysts, Wiley- VCH: Weinheim, 2011.
[7] Hulst, R.; de Vries, N. K.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 699.
[8] de Veris, A. H. M.; Meetsma, A.; Feringa, B. L. Angew. Chem. Int. Ed. Engl. 1996, 35, 2374.
[9] (a) Zhang, H.; Fang, F.; Xie, F.; Yu, H.; Yang, G.; Zhang, W. Tetrahedron Lett. 2010, 51, 3119. (b) Yang, B.; Xie, F.; Yu, H.; Shen, K.; Ma, Z.; Zhang, W. Tetrahedron 2011, 67, 6197. (c) Yu, H.; Xie, F.; Ma, Z.; Liu, Y.; Zhang, W. Org. Biomol. Chem. 2012, 10, 5137. (d) Yu, H.; Xie, F.; Ma, Z.; Liu, Y.; Zhang, W. Adv. Synth. Catal. 2012, 354, 1941.
[10] (a) Minnaard, A. J.; Feringa, B. L.; Lefort, L.; de Vries, J. G. Acc. Chem. Res. 2007, 40, 1267. (b) de Vries, A. H. M.; de Vries, J. G. Platinum Metals Rev. 2006, 50, 54.
[11] Giacomina, F.; Meetsma, A.; Panella, L.; Lefort, L.; de Vries, A. H. M.; de Vries, J. G. Angew. Chem., Int. Ed. 2007, 46, 1497.
[12] (a) Roseblade, S. J.; Pfaltz, A. Acc. Chem. Res. 2007, 40, 1402. (b) Zhang, J.; Yang, D.; Long, Y. Chin. J. Org. Chem. 2009, 29, 835 (in Chinese). (张俊芳, 杨定乔, 龙玉华, 有机化学, 2009, 29, 835.)
[13] Marie, P.; Deblon, S.; Breher, F.; Geier, J.; Böhler, C.; Rüegger, H.; Schönberg, H.; Grützmacher, H. Chem. Eur. J. 2004, 10, 4198.
[14] Broady, S. D.; Martin, D. M. G.; Lennon, I. C.; Ramsden, J. A.; Muir, J. C. WO 2006067412, 2006 [Chem. Abstr. 2006, 145, 103874].
[15] Erre, G.; Enthaler, S.; Junge, K.; Addis, D.; Beller, M. Adv. Synth. Catal. 2009, 351, 1437.
[16] Erre, G.; Junge, K.; Enthaler, S; Addis, D.; Michalik, D.; Spannenberg, A.; Beller, M. Chem. Asian J. 2008, 3, 887.
[17] Enthaler, S.; Erre, G.; Junge, K.; Schröder, K.; Addis, D.; Michalik, D.; Hapke, M.; Redkin, D.; Beller, M. Eur. J. Org. Chem. 2008, 3352.
[18] Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
[19] Hou, G.-H.; Xie, J.-H.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc. 2006, 128, 11774.
[20] Hou, G.-H.; Xie, J.-H.; Yan, P.-C.; Zhou, Q.-L. J. Am. Chem. Soc. 2009, 131, 1366.
[21] Yan, P.-C.; Xie, J.-H.; Hou, G.-H.; Wang, L.-X.; Zhou, Q.-L. Adv. Synth. Catal. 2009, 351, 3243.
[22] Yan, P.-C.; Xie, J.-H.; Zhou, Q.-L. Chin. J. Chem. 2010, 28, 1736.
[23] (a) Xiao, D.; Zhang, X. Angew. Chem., Int. Ed. 2001, 40, 3425. (b) Wang, D.-W.; Wang, X.-B.; Wang, D.-S.; Lu, S.-M.; Zhou, Y.-G.; Li, Y.-X. J. Org. Chem. 2009, 74, 2780.
[24] Blaser, H. U.; Buser, H. P.; Losers, K.; Hanreich, R.; Jalett, H. P.; Jelsch, E.; Pugin, B.; Schneider, H. D.; Splinder, F.; Wagmann, A. Chimia 1999, 53, 275.
[25] Mrši?, N.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. J. Am. Chem. Soc. 2009, 131, 8358.
[26] Hou, G.; Tao, R.; Sun, Y.; Zhang, X.; Gosselin, F. J. Am. Chem. Soc. 2010, 132, 2124.
[27] Xie, J.-H.; Yan, P.-C.; Zhang, Q.-Q.; Yuan, K.-X.; Zhou, Q.-L. ACS Catal. 2012, 2, 561.
[28] Hou, G.; Gosselin, F.; Li, W.; McWilliams, C.; Sun, Y.; Weisel, M.; O'Shea, P. D.; Chen, C.-Y.; Davies, I. W.; Zhang, X. J. Am. Chem. Soc. 2009, 131, 9882.
[29] Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2011, 112, 2557.
[30] Wang, W.-B.; Lu, S.-M.; Yang, P.-Y.; Han, X.-W.; Zhou, Y.-G. J. Am. Chem. Soc. 2003, 125, 10536.
[31] Lu, S.-M.; Han, X.-W.; Zhou, Y.-G. Adv. Synth. Catal. 2004, 346, 909.
[32] Lam, K. H.; Lu, L.; Feng, L.; Fan, Q.-H.; Lam, F. L.; Lo, W.-H.; Chan, A. S. C. Adv. Synth. Catal. 2005, 347, 1755.
[33] Reetz, M. T.; Li, X. Chem. Commun. 2006, 42, 2159.
[34] Wang, D.-W.; Zeng, W; Zhou, Y.-G. Tetrahedron: Asymmetry 2007, 18, 1103.
[35] Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683.
[36] Mrši?, N.; Lefort, L.; Boogers, J. A. F.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. Adv. Synth. Catal. 2008, 350, 1081.
[37] Mrši?, N.; Jerphagnon, T.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. Adv. Synth. Catal. 2009, 351, 2549.
[38] (a) Eggenstein, M.; Thomas, A.; Theuerkauf, J.; Franciò, G.; Leitner, W. Adv. Synth. Catal. 2009, 351, 725. (b) Hou, C.-J.; Wang, Y.-H.; Zheng, Z.; Xu, J.; Hu, X.-P. Org. Lett. 2012, 14, 3554.
[39] (a) Bess, E. N.; Sigman, M. S. Org. Lett. 2013, 15, 646. (b) Biosca, M.; Paptchikhine, A.; Pàmies, O.; Andersson, P. G.; Diéguez, M. Chem. Eur. J. 2015, 21, 3455.

亚磷酰胺配体在铱催化不对称氢化反应中的应用 2017-2018 Awarded

Applications of Phosphoramidite Ligands in Ir-Catalyzed Asymmetric Hydrogenation Reactions

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wang Jiang, Zhuangzhi Shi. Recent Progress in meta-/para-Selective Aromatic C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1691-1705.
[2]	Liqin Cao, Xiaoqin Yang, Maoqiu Li, Lin Liu, Junting Yu, Hua Tan. Synthesis and Electroluminescence Properties of Donor-Acceptor (D-A) Type Near-Infrared Iridium(III) Complex Luminescent Materials with Bipolar Transmission Features [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1831-1838.
[3]	Fei Nie, Guanbo Huang, Lei Dai, Shaofu Chen, Shaomin Ji, Jiaxiong Chen, Yanping Huo. Synthesis and Electroluminescent Properties of Red-Emitting Iridium Complexes Based on Benzofuran-Isoquinoline [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1423-1430.
[4]	Miaomiao Zhang, Bo Han, Haojie Ma, Liang Zhao, Jijiang Wang, Yuqi Zhang. Hydrosilanes as Hydrogen Source: Iridium-Catalyzed Hydrogenation of N-Heteroarenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1170-1178.
[5]	Wenqi Liu, Zhenlu Shen, Senmiao Xu. Synthesis of 1,1-Diboron Alkanes via Diborylation of Unactivated Primary C(sp³)—H Bonds Enabled by AsPh₃/Iridium Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1101-1110.
[6]	Jiahao Li, Hongqiang Liu, Bo Zhang, Bingyang Ge, Dawei Wang. Synthesis of Supported Indazolyl-Pyridyl-Quinoline Iridium Catalyst and Its Application to N-Alkylation of 2-Aminobenzothiazoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 619-630.
[7]	Huan Liu, Xufeng Lin, Da Yang. Novel Ir-Complexes for Hydroformylation of Olefins with H₂O as the Hydrogen Source [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3571-3577.
[8]	Fang Zhao, Wenjing Ye, Kai Wang. Advancement of Chiral Monodentate Phosphite Ligands in Asymmetric Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2650-2665.
[9]	Luhua Liu, Rongrong Du, Senmiao Xu. Ligand-Free Iridium-Catalyzed Borylation of Secondary Benzylic C—H Bonds [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1572-1581.
[10]	Fangfang Song, Shiyang Zhu, Hao Wang, Gong Chen. Iridium-Catalyzed Intermolecular N—N Coupling for Hydrazide Synthesis Using N-Benzoyloxycarbamates as Acyl Nitrene Precursor [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4050-4058.
[11]	Tian Fei, Zhang Jian, Yang Wulin, Deng Weiping. Progress in Iridium-Catalyzed Asymmetric Allylic Substitution Reactions via Synergetic Catalysis [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3262-3278.
[12]	Zhou Wenjing, Liu Zhiqian, Wang Zhiping, Hu Sifan, Liang Aihui. Application of Light-Emitting Electrochemical Cells Based on Cyclometalated Iridium Complexes [J]. Chin. J. Org. Chem., 2019, 39(5): 1214-1225.
[13]	Deng Yingying, Yang Wen, Yang Xin, Yang Dingqiao. Progress in Iridium-Catalyzed Asymmetric Allylic Substitution Reactions with Allylic Esters [J]. Chin. J. Org. Chem., 2017, 37(12): 3039-3059.
[14]	Yu Kunjiao, Zhang Zhenfeng, Huo Xiaohong, Wang Xingguang, Liu Delong, Zhang Wanbin. Synthesis of D-(R)-Tyrosine by Catalytic Asymmetric Hydrogenation and Its Practical Application [J]. Chin. J. Org. Chem., 2013, 33(9): 1932-1938.
[15]	ZHANG Chun-Lin, ZHANG Yu-Xiang, HU Ling-Feng, SUN Jun. Synthesis and Properties of A New Metalated Iridium Electrophos-phorescent Material Containing Carbazole-pyridazole [J]. Chin. J. Org. Chem., 2010, 30(9): 1354-1357.