Communication
Iridium‐Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes
Dedicated to the 100th anniversary of Nankai University
Abstract
The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium‐catalyzed hydroboration of aliphatic internal alkenes, providing distal‐borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate that the C−B bond of the distal‐borylated product can be readily converted into other functional groups. DFT calculations indicate that the reaction proceeds through an unexpected IrIII/IrV cycle.
Citing Literature
Number of times cited according to CrossRef: 12
- Xianjin Wang, Xin Cui, Sida Li, Yue Wang, Chungu Xia, Haijun Jiao, Lipeng Wu, Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes, Angewandte Chemie International Edition, 10.1002/anie.202002642, 59, 32, (13608-13612), (2020).
- Xianjin Wang, Xin Cui, Sida Li, Yue Wang, Chungu Xia, Haijun Jiao, Lipeng Wu, Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes, Angewandte Chemie, 10.1002/ange.202002642, 132, 32, (13710-13714), (2020).
- Dongping Wang, Yijie He, Haotian Dai, Congcong Huang, Xiang‐Ai Yuan, Jin Xie, Manganese‐Catalyzed Hydrocarbofunctionalization of Internal Alkenes†, Chinese Journal of Chemistry, 10.1002/cjoc.202000376, 38, 12, (1497-1502), (2020).
- Ronald L. Reyes, Miyu Sato, Tomohiro Iwai, Kimichi Suzuki, Satoshi Maeda, Masaya Sawamura, Asymmetric remote C–H borylation of aliphatic amides and esters with a modular iridium catalyst, Science, 10.1126/science.abc8320, 369, 6506, (970-974), (2020).
- Qing-Feng Xu-Xu, Xiao Zhang, Shu-Li You, Enantioselective Synthesis of 4-Allyl Tetrahydroquinolines via Copper(I) Hydride-Catalyzed Hydroallylation of 1,2-Dihydroquinolines, Organic Letters, 10.1021/acs.orglett.0c00113, (2020).
- Hongliang Zhao, Qian Gao, Yajuan Zhang, Panke Zhang, Senmiao Xu, Iridium-Catalyzed γ-Selective Hydroboration of γ-Substituted Allylic Amides, Organic Letters, 10.1021/acs.orglett.0c00977, (2020).
- Wei Su, Rui-Xiao Qiao, Yuan-Ye Jiang, Xiao-Li Zhen, Xia Tian, Jian-Rong Han, Shi-Ming Fan, Qiushi Cheng, Shouxin Liu, Ligand-Free Iron-Catalyzed Regioselectivity-Controlled Hydroboration of Aliphatic Terminal Alkenes, ACS Catalysis, 10.1021/acscatal.0c02731, (2020).
- Zi-Chao Wang, Di Shen, Jian Gao, Xian Jia, Youjun Xu, Shi-Liang Shi, Base-catalysed reductive relay hydroboration of allylic alcohols with pinacolborane to form alkylboronic esters, Chemical Communications, 10.1039/C9CC03459E, (2019).
- Xiaonan Shi, Sida Li, Lipeng Wu, H2‐Acceptorless Dehydrogenative Boration and Transfer Boration of Alkenes Enabled by Zirconium Catalyst, Angewandte Chemie, 10.1002/ange.201908931, 131, 45, (16313-16317), (2019).
- Xiaonan Shi, Sida Li, Lipeng Wu, H2‐Acceptorless Dehydrogenative Boration and Transfer Boration of Alkenes Enabled by Zirconium Catalyst, Angewandte Chemie International Edition, 10.1002/anie.201908931, 58, 45, (16167-16171), (2019).
- Feng Li, Xu Bai, Yuan Cai, Han Li, Shuo-Qing Zhang, Feng-Hua Liu, Xin Hong, Youjun Xu, Shi-Liang Shi, Aluminum-Catalyzed Selective Hydroboration of Alkenes and Alkynylsilanes, Organic Process Research & Development, 10.1021/acs.oprd.9b00205, (2019).
- Xiao-Yan Bai, Wei Zhao, Xin Sun, Bi-Jie Li, Rhodium-Catalyzed Regiodivergent and Enantioselective Hydroboration of Enamides, Journal of the American Chemical Society, 10.1021/jacs.9b10578, (2019).
