Palladium-Catalyzed One-Step Synthesis of Stereodefined Difunctionalized Glycals  

作　　者：Xiao-Ping Gong Yuke Li Hong-Chao Liu Zhe Zhang Zhi-Jie Niu Ya-Nan Ding Yang An Xi Chen Yan-Chong Huang Rui-Qiang Jiao Xue-Yuan Liu Yong-Min Liang 

机构地区：[1]State Key Laboratory of Applied Organic Chemistry,Lanzhou University,Lanzhou 730000 [2]Department of Chemistry,Centre for Scientific Modeling and Computation,Chinese University of Hong Kong,Shatin,Hong Kong 999077

出　　处：《CCS Chemistry》2023年第3期741-749,共9页中国化学会会刊（英文）

基　　金：We thank the National Natural Science Foundation of China(NSF 22171114 and 21772075)for its financial support.

摘　　要：Efficiently modifying glycals by directly introducing functional groups into their double bonds is a longstanding challenge.Here,the strategy of introducing two different functional groups into 1-iodoglycals to obtain modified glycals in one step through palladium catalysis was reported for the first time,and the modified glycals contained stereodefined tetrasubstituted olefins.Using this method,various difunctionalized glycals that were difficult to form by other routes were synthesized in moderate to good yields.Control experiments and density functional theory calculations show that the palladium catalyst played dual roles in this transformation,namely,inducing nucleophilic substitution and catalyzing Suzuki coupling.The reaction intermediate was isolated and confirmed by X-ray crystallographic analysis.Furthermore,the gram-scale synthesis and facile deprotection of the target compound enhances the practicality of this strategy.

关 键 词：palladium catalysis GLYCALS tetrasubstitute olefins difunctionalization stereodefined threecomponent 

分 类 号：TQ426[化学工程]