Enantioselective α-C(sp<sup>3</sup>)–H Borylation of Masked Primary Alcohols Enabled by Iridium Catalysis
Functional group-directed site- and enantioselective C(sp<sup>3</sup>)-H functionalization of alcohols or masked alcohols represents a formidable challenge. We herein report the first example of iridium-catalyzed asymmetric α-C(sp<sup>3</sup>)-H borylation of primary alcohol-derived carbamates by the judicious choice of directing groups. A variety of chiral borylated carbamates were obtained with good to high enantioselectivities. We also demonstrated the synthetic utility by taking advantage of the highly transformable feature of C-B bonds and the leaving ability of carbamates.
Authors
- Xiangfeng Shao (ORCID: https://orcid.org/0000-0002-8710-4122)
- Senmiao Xu (ORCID: https://orcid.org/0000-0003-0249-8765)
- Zhuofeng Ke (ORCID: https://orcid.org/0000-0001-9064-8051)
- Yinwu Li (ORCID: https://orcid.org/0000-0002-3472-3413)
- Lili Chen (ORCID: https://orcid.org/0000-0003-0936-8592)
- Qian Gao (ORCID: https://orcid.org/0000-0001-5457-1376)
- Liangjun Xie
Institutions
- Sun Yat-sen University (CN)
- Hangzhou Normal University (CN)
- Chinese Academy of Sciences (CN)
- Lanzhou Institute of Chemical Physics (CN)
- University of Chinese Academy of Sciences (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2024-12-19
- DOI
- https://doi.org/10.1021/jacs.4c14890
- Citations
- 7
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.75
Funders
- National Natural Science Foundation of China
- Hangzhou Normal University
- Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences
- National Key Research and Development Program of China
- Basic and Applied Basic Research Foundation of Guangdong Province