Citation: He Yao, Wenhao Ji, Yi Feng, Chunbo Qian, Chengguang Yue, Yue Wang, Shouying Huang, Mei-Yan Wang, Xinbin Ma. Copper-catalyzed and biphosphine ligand controlled 3,4-boracarboxylation of 1,3-dienes with carbon dioxide[J]. Chinese Chemical Letters, ;2025, 36(4): 110076. doi: 10.1016/j.cclet.2024.110076 shu

Copper-catalyzed and biphosphine ligand controlled 3,4-boracarboxylation of 1,3-dienes with carbon dioxide

He Yao ^{a, 1} ,
Wenhao Ji ^{a, 1} ,
Yi Feng ^a ,
Chunbo Qian ^a ,
Chengguang Yue ^a ,
Yue Wang ^a ,
Shouying Huang ^{a, b} ,
Mei-Yan Wang ^{a, b, *,} ,
Xinbin Ma ^{a, *,}

a.
School of Chemical Engineering and Technology, Key Laboratory for Green Chemical Technology of Ministry of Education, Collaborative Innovation Center of Chemical Science and Engineering, Tianjin University, Tianjin 300072, China
b.
Ningbo Key Laboratory of Green Petrochemical Carbon Emission Reduction Technology and Equipment, Zhejiang Institute of Tianjin University, Ningbo 315200, China

mywang2017@tju.edu.cn

xbma@tju.edu.cn

Received Date: 16 April 2024
Revised Date: 15 May 2024
Accepted Date: 30 May 2024
Available Online: 31 May 2024

Figures(9)

A strategy for copper-catalyzed and biphosphine ligand controlled boracarboxylation of 1,3-dienes and CO₂ with 3,4-selectivity was developed. The CuCl coupled with DPPF (1,1′-bis(diphenylphosphino)ferrocene) was assigned to be the best catalyst, with 84% yield and exclusive 3,4-selectivity. The ligand effect on both catalytic activity and regioselectivity of boracarboxylation was disclosed, which is rarely reported in any copper catalyzed boracarboxylation. The borocupration process is revealed to be a vital step for the biphosphine participated boracarboxylation of 1,3-dienes with CO₂. The minimal substrate distortion occurring in 3,4-borocupration favors the 3,4-regioselectivity of boracarboxylation. The “pocket” confinement and suitable β_n (92°–106°) of bisphosphine ligands are demonstrated to be in favour of the interaction between LCu-Bpin complex (the catalytic precursor) and 1,3-diene substrate to decrease their interaction energy ∆E_int(ζ) in 3,4-borocupration, thus promoting the 3,4-boracarboxylation.
- Carbon dioxide,
- Ligand effect,
- Carboxylation,
- β,γ-Unsaturated carboxylic acid,
- DFT calculation
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