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

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Abstract：

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　C[sbnd]H　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.　©　2023

Keyword：

Carbohydrate C-glycals Glycosyl stannanes Stille coupling Sulfonium salts Synergistic catalysis

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[ 1 ] [Yan W.]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 2 ] [Zheng M.]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 3 ] [Chuang P.]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 4 ] [Sun H.]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 5 ] [Wang S.]National Engineering Research Center of Chemical Fertilizer Catalyst, College of Chemical Engineering, Fuzhou University, Fuzhou, 350108, China
[ 6 ] [Xu C.]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 7 ] [Chen F.-E.]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 8 ] [Chen F.-E.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai, 200433, China
[ 9 ] [Chen F.-E.]Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Fudan University, Shanghai, 200433, China

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

Chinese Chemical Letters

ISSN： 1001-8417

Year： 2023

Issue： 7

Volume： 34

9 . 4

JCR@2023

9 . 4 0 0

JCR@2023

ESI HC Threshold：39

JCR Journal Grade：1

CAS Journal Grade：2

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SCOPUS Cited Count：

ESI Highly Cited Papers on the List： 0 Unfold All

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Chinese Cited Count：

30 Days PV： 1

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