Application of Pinacolborane in Catalytic Enantioselective Hydroboration of Ketones and Imines

doi:10.6023/cjoc202008039

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3596-3604.DOI: 10.6023/cjoc202008039 Previous Articles Next Articles

Special Issue: 创刊四十周年专辑

频哪醇硼烷在酮及亚胺的不对称硼氢化中的应用

刘文伯, 陆展

浙江大学化学系杭州 310000

收稿日期:2020-08-21 修回日期:2020-09-08 发布日期:2020-09-16
通讯作者: 陆展 E-mail:luzhan@zju.edu.cn
基金资助:
国家自然科学基金（Nos.21922107，21772771）、浙江省自然科学基金（No.LR19B020001）、浙江大学化学前瞻技术研究中心和中央高校基本科研业务费（No.2019QNA3008）资助项目.

Application of Pinacolborane in Catalytic Enantioselective Hydroboration of Ketones and Imines

Liu Wenbo, Lu Zhan

Department of Chemistry, Zhejiang University, Hangzhou 310000

Received:2020-08-21 Revised:2020-09-08 Published:2020-09-16
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21922107, 21772171), the Natural Science Foundation of Zhejiang Province (No. LR19B020001), the Center of Chemistry for Frontier Technologies and the Fundamental Research Funds for the Central Universities (No. 2019QNA3008).

Enantioselective hydroboration of ketones and imines provides a powerful method to access valuable chiral alcohols and amines which are widely used in organic synthesis, materials science, pharmaceutical, agrochemistry and fine chemical industry. After invented in 1991, pinacolborane (HBpin) as a stable, commercially available and measurably simple reductive reagent has been widely applied in hydroboration of carbonyl derivatives, imines and nitriles and relevant mechanistic investigation. In the past 5 years, HBpin has also been employed for asymmetric catalytic hydroboration (CHB) to access chiral alcohols and amines. The enantioselective CHB reactions of ketones and imines using HBpin are outlined according to the classification of different catalysts, such as earth abundant transition metals, main group elements, and rare-earth metals.

Key words: pinacolborane, asymmetric hydroboration, earth abundant transition metal, ketone, imine

Cite this article

Liu Wenbo, Lu Zhan. Application of Pinacolborane in Catalytic Enantioselective Hydroboration of Ketones and Imines[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3596-3604.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Marsden, S. Boronic Acids:Preparation and Applications in Organic Synthesis, Medicine and Materials, Vols. 1 and 2, Ed.:Hall, D. G., Wiley-VCH, Weinheim, 2011.
[2] Chong, C. C.; Kinjo, R. ACS Catal. 2015, 5, 3238.
[3] Brown, H. C.; Schlesinger, H. I.; Burg, A. B. J. Am. Chem. Soc. 1939, 61, 673.
[4] Wang, Z. In Comprehensive Organic Name Reactions and Reagents, Ed.:Wang, Z., John Wiley & Sons, New Jersey, 2010, pp. 536~543.
[5] Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986.
[6] Tucker, C. E.; Davidson, J.; Knochel, P. J. Org. Chem. 1992, 57, 3482.
[7] Shegavi, M. L.; Bose, S. K. Catal. Sci. Technol. 2019, 9, 3307.
[8] Koren-Selfridge, L.; Londino, H. N.; Vellucci, J. K.; Simmons, B. J.; Casey, C. P.; Clark, T. B. Organometallics 2009, 28, 2085.
[9] Query, I. P.; Squier, P. A.; Larson, E. M.; Isley, N. A.; Clark, T. B. J. Org. Chem. 2011, 76, 6452.
[10] Wu, Y.; Shan, C.; Ying, J.; Su, J.; Zhu, J.; Liu, L. L.; Zhao, Y. Green Chem. 2017, 19, 4169.
[11] Guo, J.; Chen, J.; Lu, Z. Chem. Commun. 2015, 51, 5725.
[12] Adams, M. R.; Tien, C.-H.; McDonald, R.; Speed, A. W. H. Angew. Chem., Int. Ed. 2017, 56, 16660.
[13] Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed., 2001, 40, 40.
[14] Liu, W.; Guo, J.; Xing, S.; Lu, Z. Org. Lett. 2020, 22, 2532.
[15] Chen, F.; Zhang, Y.; Yu, L.; Zhu, S. Angew. Chem., Int. Ed. 2017, 56, 2022.
[16] Vasilenko, V.; Blasius, C. K.; Wadepohl, H.; Gade, L. H. Angew. Chem., Int. Ed. 2017, 56, 8393.
[17] Vasilenko, V.; Blasius, C. K.; Gade, L. H. J. Am. Chem. Soc. 2018, 140, 9244.
[18] Blasius, C. K.; Vasilenko, V.; Gade, L. H. Angew. Chem., Int. Ed. 2018, 57, 10231.
[19] Blasius, C. K.; Heinrich, N. F.; Vasilenko, V. Gade, L. H. Angew. Chem., Int. Ed. 2020, 59, 15974.
[20] Agarwal, R.; Liao, Y.; Lin, D.-J.; Yang, Z.-X.; Lai, C.-F.; Chen, C.-T. Org. Chem. Front. 2020, 7, 2505.
[21] Mukherjee, D.; Osseili, H.; Spaniol, T. P.; Okuda, J. J. Am. Chem. Soc. 2016, 138, 10790.
[22] Willcox, D.; Carden, J. L.; Ruddy, A. J.; Newman, P. D.; Melen, R. L. Dalton Trans. 2020, 49, 2417.
[23] Falconnet, A.; Magre, M.; Maity, B.; Cavallo, L.; Rueping, M. Angew. Chem., Int. Ed. 2019, 58, 17567.
[24] Vasilenko, V.; Blasius, C. K.; Wadepohl, H.; Gade, L. H. Chem. Commun. 2020, 56, 1203.
[25] Lebedev, Y.; Polishchuk, I.; Maity, B.; Guerreiro, M. D. V.; Cavallo, L.; Rueping, M. J. Am. Chem. Soc. 2019, 141, 19415.
[26] Lundrigan, T.; Welsh, E. N.; Hynes, T.; Tien, C.-H.; Adams, M. R.; Roy, K. R.; Robertson, K. N.; Speed, A. W. H. J. Am. Chem. Soc. 2019, 141, 14083.
[27] Tian, J.-J.; Yang, Z.-Y.; Liang, X.-S.; Liu, N.; Hu, C.-Y.; Tu, X.-S.; Li, X.; Wang, X.-C. Angew. Chem., Int. Ed. 2020, 59, 18452.
[28] Song, P.; Lu, C.; Fei, Z.; Zhao, B.; Yao, Y. J. Org. Chem. 2018, 83, 6093.
[29] Sun, Y.; Lu, C.; Zhao, B.; Xue, M. J. Org. Chem. 2020, 85, 10504.
[30] Zhang, F.-H.; Zhang, F.-G.; Li, M.-L.; Xie, J.-H.; Zhou, Q.-L. Nat. Catal. 2020, 3, 621.
[31] For recent reactions with other boranes:(a) Taniguchi, T.; Curran, D. P. Angew. Chem., Int. Ed. 2014, 53, 13150.
(b) Zhou, N.; Yuan, X.-A.; Zhao, Y.; Xie, J.; Zhu, C. Angew. Chem., Int. Ed. 2018, 57, 3990.
(c) Shimoi, M.; Watanabe, T.; Maeda, K.; Curran, D. P.; Taniguchi, T. Angew. Chem., Int. Ed. 2018, 57, 9485.
(d) Yamamoto, K.; Mohara, Y.; Mutoh, Y.; Saito, S. J. Am. Chem. Soc. 2019, 141, 17042.
(e) Dai, W.; Geib, S. J.; Curran, D. P. J. Am. Chem. Soc. 2020, 142, 6261.
[32] For selected reviews:(a) Chen, J.; Lu, Z. Org. Chem. Front. 2018, 5, 260.
(b) Chen, J.; Guo, J.; Lu, Z. Chin. J. Chem. 2018, 36, 1075.
(c) Cheng, Z.; Guo, J.; Lu, Z. Chem. Commun. 2020, 56, 2229.
(d) Li, Y. Y.; Cheng, Y. H.; Shan, C. H.; Zhang, J.; Xu, D. D.; Bai, R. P.; Qu, L. B.; Lan, Y. Chin. J. Org. Chem. 2018, 38, 1885(in Chinese). (李园园, 程玉华, 单春晖, 张敬, 徐冬冬, 白若鹏, 屈凌波, 蓝宇, 有机化学, 2018, 38, 1885.)
(e) Sun, Y.; Guan, R.; Liu, Z. H.; Wang, Y. M. Chin. J. Org. Chem. 2020, 40, 651(in Chinese). (孙越, 关瑞, 刘兆洪, 王也铭, 有机化学, 2020, 40, 651.)

频哪醇硼烷在酮及亚胺的不对称硼氢化中的应用

Application of Pinacolborane in Catalytic Enantioselective Hydroboration of Ketones and Imines

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hu Ma, Danfeng Huang, Kehu Wang, Duoduo Tang, Yang Feng, Yuanyuan Reng, Junjiao Wang, Yulai Hu. Synthesis of 3-Trifluoromethylpyrazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3257-3267.
[2]	Junjie Zhang, Xuetao Xu. [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3297-3303.
[3]	Xiaoke Zhang, Xiangru Zheng, Chaoyong Wang. Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3180-3187.
[4]	Min Liu, Dongyan Yang, Yumei Xiao, Wangcang Su, Fenghai Zhao, Qin Zhaohai .. Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2790-2799.
[5]	Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960.
[6]	Wenqian Wu, Chunxia Chen, Jinsong Peng, Zhanyu Li. Research Progress of Carbonyl α-Position Amination [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2743-2763.
[7]	Xingxing Yang, Yonghao Fan, Jingjing Cui. Recent Progress in the Main Group Complexes with the 2,6-Pyridinediimine [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2338-2350.
[8]	Lixing Sun, Tingting Sun, Haiqing Wang, Shufang Wu, Xiaoye Wang, Tianya Liu, Yuchen Zhang. Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2178-2188.
[9]	Miaomiao Zhang, Rong Chen, Hongmei Jiao, Haojie Ma, Bo Han, Yuqi Zhang, Jijiang Wang. MgCl₂-Catalyzed Chemoselective Reduction of Aldehydes, Ketones and Imines [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1462-1471.
[10]	Tingting Liu, Yucai Hu, An Shen. Mechanism of Carbon-Carbon Coupling Reactions Catalyzed by Imine-Ligand-Assisted N-Heterocyclic Carbene Palladium Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 622-628.
[11]	Yongling Wang, Tiexin Zhang, Xuming Zhang, Hanyang Sun, Jinyao Leng, Yaming Li. Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4284-4293.
[12]	Peng Zhou, Weiming Zhu, Jiantao Zhang, Duoduo Xiao, Xiangfeng Guo, Weibing Liu. Cobalt-Catalyzed Oxyalkylation Reaction of Styrenes: Rapid Access to α-Alkyl Substituted Acetophenone Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3939-3944.
[13]	Yuehua Zhang, Fei Nie, Lu Zhou, Xiaofeng Wang, Yuan Liu, Yanping Huo, Wencheng Chen, Zujin Zhao. Synthesis and Optoelectronic Studies of Thermally Activated Delayed Fluorescence Materials Based on Benzothiazolyl Ketones [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3876-3887.
[14]	Duoduo Xiao, Jiantao Zhang, Peng Zhou, Weibing Liu. Metal-Free α-C(sp³)—H Methylenation of Aryl Ketones to Form γ-Keto Sulfoxides with Dimethyl Sulfoxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3900-3906.
[15]	Yunpeng Qi, Dengkai Lin, Liang-An Chen. Research Progress on Reductive Acylation with Acyl-Ni as a Key Intermediate to Synthesize Ketones [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3861-3875.