Volume 38, Issue 12
Concise Report

Iridium‐Catalyzed Enantioselective C(sp3)–H Borylation of Cyclobutanes

Xiang Chen

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014 China

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 China

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Lili Chen

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 China

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Hongliang Zhao

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 China

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Qian Gao

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 China

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Zhenlu Shen

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014 China

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Senmiao Xu

Corresponding Author

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 China

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, 311121 China

E‐mail: senmiaoxu@licp.cas.cnSearch for more papers by this author
First published: 01 June 2020
Citations: 3

Summary of main observation and conclusion

We herein report the first example of iridium‐catalyzed enantioselective C(sp3)–H borylation of cyclobutanes using benzoxazoline as the directing group. The combination of a chiral bidentate boryl ligand and an iridium precursor has found to effectively catalyze C(sp3)–H borylation to afford a variety of cyclobutylboronates with good to excellent enantioselectivities. We also demonstrate the synthetic utility of the current method by converting the stereogenic C—B bond to other functionalities.

Number of times cited according to CrossRef: 3

  • Advances in the catalytic asymmetric synthesis of quaternary carbon containing cyclobutanes, Organic Chemistry Frontiers, 10.1039/D0QO00685H, (2020).
  • Iridium‐Catalyzed Enantioselective Unbiased Methylene C(sp3)–H Borylation of Acyclic Amides, Angewandte Chemie, 10.1002/ange.202013568, 0, 0, (2020).
  • Iridium‐Catalyzed Enantioselective Unbiased Methylene C(sp3)–H Borylation of Acyclic Amides, Angewandte Chemie International Edition, 10.1002/anie.202013568, 0, 0, (2020).

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