Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2019, 141, 27, 10599-10604
Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)–H Borylation of Cyclopropanes
- Yongjia ShiYongjia ShiState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, ChinaUniversity of Chinese Academy of Sciences, Beijing 100049, ChinaMore by Yongjia Shi,
- Qian GaoQian GaoState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, ChinaMore by Qian Gao, and
- Senmiao Xu*Senmiao Xu*[email protected]State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, ChinaKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, ChinaMore by Senmiao Xu
Abstract
We herein report an Ir-catalyzed enantioselective C(sp3)–H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the first time. A variety of substrates with α-quaternary carbon centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. We have also demonstrated that the borylated products can be used as versatile precursors engaging in stereospecific transformations of C–B bonds, including the synthesis of a bioactive compound Levomilnacipran.
Cited By
This article is cited by 16 publications.
- Łukasz Woźniak, Jin-Fay Tan, Qui-Hien Nguyen, Adrien Madron du Vigné, Vitalii Smal, Yi-Xuan Cao, Nicolai Cramer. Catalytic Enantioselective Functionalizations of C–H Bonds by Chiral Iridium Complexes. Chemical Reviews 2020, 120 (18) , 10516-10543. https://doi.org/10.1021/acs.chemrev.0c00559
- You-Ke Chen, Yan-Shang Kang, Hua-Jin Xu, Ping Zhang, Jing Zhao, Tiantian Li, Wei-Yin Sun, Yi Lu. Rh(III)-Catalyzed C(sp3)–H Acetoxylation of 8-Methylquinolines. Organic Letters 2020, 22 (14) , 5390-5395. https://doi.org/10.1021/acs.orglett.0c01715
- Lili Chen, Yuhuan Yang, Luhua Liu, Qian Gao, Senmiao Xu. Iridium-Catalyzed Enantioselective α-C(sp3)–H Borylation of Azacycles. Journal of the American Chemical Society 2020, 142 (28) , 12062-12068. https://doi.org/10.1021/jacs.0c06756
- Margaret R. Jones, Caleb D. Fast, Nathan D. Schley. Iridium-Catalyzed sp3 C–H Borylation in Hydrocarbon Solvent Enabled by 2,2′-Dipyridylarylmethane Ligands. Journal of the American Chemical Society 2020, 142 (14) , 6488-6492. https://doi.org/10.1021/jacs.0c00524
- Ronald L. Reyes, Miyu Sato, Tomohiro Iwai, Masaya Sawamura. Asymmetric Synthesis of α-Aminoboronates via Rhodium-Catalyzed Enantioselective C(sp3)–H Borylation. Journal of the American Chemical Society 2020, 142 (1) , 589-597. https://doi.org/10.1021/jacs.9b12013
- Jian-Jun Feng, Wenbin Mao, Liangliang Zhang, Martin Oestreich. Activation of the Si–B interelement bond related to catalysis. Chemical Society Reviews 2021, 113 https://doi.org/10.1039/D0CS00965B
- Yuhuan Yang, Lili Chen, Senmiao Xu. Iridium‐Catalyzed Enantioselective Unbiased Methylene C(sp 3 )–H Borylation of Acyclic Amides. Angewandte Chemie International Edition 2020, 131 https://doi.org/10.1002/anie.202013568
- Yuhuan Yang, Lili Chen, Senmiao Xu. Iridium‐Catalyzed Enantioselective Unbiased Methylene C(sp 3 )–H Borylation of Acyclic Amides. Angewandte Chemie 2020, 131 https://doi.org/10.1002/ange.202013568
- Yin‐Xia Wang, Ping‐Feng Zhang, Mengchun Ye. Well‐Designed Chiral Ligands for Enantioselective Ir‐Catalyzed C(sp 2 )–H Borylation †. Chinese Journal of Chemistry 2020, 38 (12) , 1762-1766. https://doi.org/10.1002/cjoc.202000288
- Xiang Chen, Lili Chen, Hongliang Zhao, Qian Gao, Zhenlu Shen, Senmiao Xu. Iridium‐Catalyzed Enantioselective C(sp 3 )–H Borylation of Cyclobutanes. Chinese Journal of Chemistry 2020, 38 (12) , 1533-1537. https://doi.org/10.1002/cjoc.202000240
- Xiao Sun, Peiming Gu, Jiao Qin, Yan Su. Rhodium-catalysed diastereo- and enantio-selective cyclopropanation of α-boryl styrenes. Chemical Communications 2020, 56 (82) , 12379-12382. https://doi.org/10.1039/D0CC02549F
- Yan Li, Xiu-Fen Cheng, Fan Fei, Tian-Rui Wu, Kang-Jie Bian, Xin Zhou, Xi-Sheng Wang. Palladium( ii )-catalyzed asymmetric C–H carbonylation to diverse isoquinoline derivatives bearing all-carbon quaternary stereocenters. Chemical Communications 2020, 56 (78) , 11605-11608. https://doi.org/10.1039/D0CC05219A
- Miao Zhan, Peidong Song, Jiao Jiao, Pengfei Li. Novel Chiral Ligands‐Enabled Transition‐Metal‐Catalyzed Asymmetric C—H Borylation. Chinese Journal of Chemistry 2020, 38 (6) , 665-667. https://doi.org/10.1002/cjoc.202000023
- Wubing Yao, Jianguo Yang, Feiyue Hao. Ru‐Catalyzed Selective C(sp 3 )−H Monoborylation of Amides and Esters. ChemSusChem 2020, 13 (1) , 121-125. https://doi.org/10.1002/cssc.201902448
- Elena Fernández. Iridium-Catalyzed Undirected Homogeneous C–H Borylation Reaction. 2020,,https://doi.org/10.1007/3418_2020_53
- Kazuhiko Semba, Ikuya Fujii, Yoshiaki Nakao. A PAlP Pincer Ligand Bearing a 2-Diphenylphosphinophenoxy Backbone. Inorganics 2019, 7 (12) , 140. https://doi.org/10.3390/inorganics7120140