Citation: Wujun Jian, Mong-Feng Chiou, Yajun Li, Hongli Bao, Song Yang. Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes[J]. Chinese Chemical Letters, ;2024, 35(5): 108980. doi: 10.1016/j.cclet.2023.108980 shu

Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes

Wujun Jian ^a ,
Mong-Feng Chiou ^b ,
Yajun Li ^{c, *,} ,
Hongli Bao ^{c, *,} ,
Song Yang ^{a, *,}

a.
National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China
b.
Strait Institute of Flexible Electronics (SIFE, Future Technologies), Fujian Normal University, Fuzhou 350117, China
c.
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou 350002, China

liyajun@fjirsm.ac.cn

hlbao@fjirsm.ac.cn

syang@gzu.edu.cn

Received Date: 31 May 2023
Revised Date: 14 August 2023
Accepted Date: 24 August 2023
Available Online: 27 August 2023

Figures(5)

Borylation of 1,3-enynes with bis(boronate) compounds often ends up with the formation of hydroborylated products, leaving the diborylation of 1,3-enynes for the formation of 1,4-diborylated allenes to be challenging. Herein, a copper-catalyzed chemo-, regio-, and stereo-selective diborylation of 1,3-enynes for the efficient construction of 1,4-diborylated allenes under base-free conditions was reported. A wide range of 1,3-enynes bearing various functional groups can participant in the reaction and afforded the corresponding 1,4-diborylated allenes in good to excellent yields, which was enabled by the protocol of Bpin to BF₃K conversion. the borylcopper species was supposed to selectively attack the C–C triple bond of the 1,3-enynes.
- Copper catalysis,
- Regioselective,
- 1,3-Enynes,
- Borylation,
- Allenes
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