A Copper-Catalyzed[5+1]Cycloaddition of Terminal Alkynes with Diazo Esters through a Tandem 1,5-H-Shift Cyclization  

作　　者：Tonggang Hao Min Shi Yin Wei 

机构地区：[1]State Key Laboratory of Organometallic Chemistry,Center for Excellence in Molecular Synthesis,University of Chinese Academy of Sciences,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,345 Lingling Road,Shanghai,200032 China

出　　处：《Chinese Journal of Chemistry》2023年第3期301-306,共6页中国化学（英文版）

基　　金：support from the National Natural Science Foundation of China (Nos.21372250,21121062,21302203,20732008,21772037,21772226,21861132014,91956115,and 22171078).

摘　　要：A copper-catalyzed[5+1]cycloaddition reaction of terminal alkynes with diazo esters for the rapid construction of protected naphthalen-1(2H)-one derivatives in moderate to good yields has been disclosed along with good functional group compatibility and a broad substrate scope.The mechanistic investigations reveal that this tandem cyclization process proceeds through a Cu(I)-catalyzed coupling of terminal alkyne with diazoacetate,a 1,5-H shift process and a thermally induced pericyclic reaction via an allene intermediate.The synthetic utility and the further transformations of the obtained cycloadduct to naphthalenone,naphthol and dihydronaphthol have been also presented in this paper.

关 键 词：[5+1]Cycloaddition Diazo ester 1 5-H-shift One-pot synthesis Copper catalyzed 

分 类 号：O62[理学—有机化学]