Citation: Yuanhong Cai, Donghang Tan, Qiqi Zhang, Wenxin Lv, Qingjiang Li, Honggen Wang. Synthesis of difluoromethylated benzylborons via rhodium(I)-catalyzed fluorine-retainable hydroboration of gem-difluoroalkenes[J]. Chinese Chemical Letters, ;2021, 32(1): 417-420. doi: 10.1016/j.cclet.2020.03.031 shu

Synthesis of difluoromethylated benzylborons via rhodium(I)-catalyzed fluorine-retainable hydroboration of gem-difluoroalkenes

Yuanhong Cai ^a ,
Donghang Tan ^a ,
Qiqi Zhang ^a ,
Wenxin Lv ^a ,
Qingjiang Li ^a ,
Honggen Wang ^{a, b, *,}

a.
Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China
b.
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, China

wanghg3@mail.sysu.edu.cn

Received Date: 9 February 2020
Revised Date: 1 March 2020
Accepted Date: 11 March 2020
Available Online: 13 March 2020

Figures(4)

The synthesis of borylated organofluorines is of great interest due to their potential values as synthons in modular construction of fluorine-containing molecules. Reported herein is a rhodium-catalyzed hydroboration of aryl gem-difluoroalkenes leading to a series of α-difluoromethylated benzylborons. The use of cationic rhodium catalyst and a biphosphine ligand with large bite angle was crucial for reactivity by offering good regioselectivity and diminishing the undesired β-F elimination. Preliminary derivatizations of the products were conducted to showcase the utility of this protocol.
- Rhodium,
- Hydroboration,
- Difluoromethy,
- gem-Difluoroalkene,
- β-F elimination
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