Citation: Peng Guo, Shicheng Dong, Xiang-Gui Zhang, Bing-Bin Yang, Jun Zhu, Ke-Yin Ye. Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates[J]. Chinese Chemical Letters, ;2025, 36(4): 110052. doi: 10.1016/j.cclet.2024.110052 shu

Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates

Peng Guo ^{a, 1} ,
Shicheng Dong ^{c, 1} ,
Xiang-Gui Zhang ^a ,
Bing-Bin Yang ^a ,
Jun Zhu ^{b, c, *,} ,
Ke-Yin Ye ^{a, *,}

a.
College of Chemistry, Fuzhou University, Fuzhou 350108, China
b.
School of Science and Engineering, The Chinese University of Hong Kong, Shenzhen 518172, China
c.
State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China

jun.zhu@cuhk.edu.cn

kyye@fzu.edu.cn

Received Date: 8 March 2024
Revised Date: 13 May 2024
Accepted Date: 24 May 2024
Available Online: 25 May 2024

Figures(9)

In most Suzuki–Miyaura carbon-carbon cross-coupling reactions, the borabicyclo[3.3.1]nonane scaffold (9-BBN) only serves as an auxiliary facilitating the transmetalation step and thus is transformed into by-products. There are rare examples where the 9-BBN derivatives serve as the potentially diverse C8 building blocks in cross-coupling reactions. Herein, we report a cobalt-catalyzed migratory carbon-carbon cross-coupling reaction of the in situ formed 9-BBN ate complexes to afford diverse aryl- and alkyl-functionalized cyclooctenes. Preliminary mechanistic studies suggest the oxidation-induced cis-bicyclo[3.3.0]oct-1-ylborane is the key intermediate in this migratory cross-coupling reaction, which promotes the development of other diverse migratory cross-coupling of borate complexes.
- Cobalt,
- Cross-coupling,
- Borate,
- Rearrangement,
- Cyclooctene
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