Rh-Catalyzed Reaction of Propargylic Alcohols with Aryl Boronic Acids-Switch from β-OH Elimination to Protodemetalation  

作　　者：Weiyi Wang Hui Qian Shengming Ma 

机构地区：[1]Research Center for Molecular Recognition and Synthesis,Deportment of Chemistry,Fudan University,220 Handan Lu,Shanghai 200433,China [2]State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,345 Lingling Lu,Shanghai 200032,China

出　　处：《Chinese Journal of Chemistry》2020年第4期331-345,共15页中国化学（英文版）

基　　金：Financial support from the National Natural Science Founda-tion of China(Grant No.21690063 for S.Ma and Grant No.21801041 for H.Qian)and the National Basic Research Program(2015CB856600 for S.Ma)is greatly appreciated.We thank Mr.Yizhan Zhai in this group for reproducing the results for E-3ad,E-3fi and(R)-E-3fb as presented in this study.

摘　　要：Summary of main observation and conclusion It is known that Rh-catalyzed reaction of propargyic alcohols with aryl metallic reagents undergoes Su2Z-type reaction affording alenes via a sequential arylmetalation andβ-OH elimination process.Here we report a Rh/Ag cocatalyed reaction of pro-pargylic alcohols with organoboronic acids affording stereo defined(E)-3-arlallylic alcohols via arylmetalation and protodemetalation with a high regio-and stereoselectivity under very mild conditions.The reaction exhibits a good substrate scope and the compatibility with synthetically useful functional groups with no racemization for optically active propargylic alcohols.Such a reaction may also be extended to homopropargylie alcohols with a remarka-ble regioselectivity and exclusive E-stereoselectity.

关 键 词：process. ALCOHOLS afford 

分 类 号：O62[理学—有机化学]