Citation: Weitao Yan, Mingwen Zheng, Peihsuan Chuang, Hao Sun, Shiping Wang, Chunfa Xu, Fen-Er Chen. Synergistic Pd/Cu catalysis enabled cross-coupling of glycosyl stannanes with sulfonium salts to access C-aryl/alkenyl glycals[J]. Chinese Chemical Letters, ;2023, 34(7): 108021. doi: 10.1016/j.cclet.2022.108021 shu

Synergistic Pd/Cu catalysis enabled cross-coupling of glycosyl stannanes with sulfonium salts to access C-aryl/alkenyl glycals

Weitao Yan ^a ,
Mingwen Zheng ^a ,
Peihsuan Chuang ^a ,
Hao Sun ^a ,
Shiping Wang ^{b, *,} ,
Chunfa Xu ^{a, *,} ,
Fen-Er Chen ^{a, c, d, *,}

a.
Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China
b.
National Engineering Research Center of Chemical Fertilizer Catalyst, College of Chemical Engineering, Fuzhou University, Fuzhou 350108, China
c.
Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China
d.
Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Fudan University, Shanghai 200433, China

wangsp@fzu.edu.cn

xucf@fzu.edu.cn

rfchen@fudan.edu.cn

Received Date: 28 September 2022
Revised Date: 20 November 2022
Accepted Date: 23 November 2022
Available Online: 26 November 2022

Figures(6)

A highly efficient coupling of glycosyl stannanes and sulfonium salts enabled by synergistic Pd/Cu catalysis is disclosed, facilitating the construction of C-aryl/alkenyl glycals under mild conditions in high yields. The protocol tolerates a wide scope of functional groups including ketone, cyano, ester, amide, nitro, halide. The one-pot formal CH glycosylation starting from arene is demonstrated with a reaction sequence of dibenzothiophenylation/Stille coupling. Besides, a gram-scale reaction is performed successfully, showing the high applicability of this protocol.
- C-glycals,
- Sulfonium salts,
- Synergistic catalysis,
- Carbohydrate,
- Glycosyl stannanes,
- Stille coupling
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