Trimerization of Acetylene and Alkene:Rapid Access to Polyenes  

作　　者：Boxiang Liu Zhicong Lin Yu Wang Tairan Cheng Tongxiang Cao Shifa Zhu 

机构地区：[1]Key Laboratory of Functional Molecular Engineering of Guangdong Province,School of Chemistry and Chemical Engineering,South China University of Technology,Guangzhou 510640 [2]State Key Laboratory of Elemento-Organic Chemistry,Nankai University,Tianjin 300071

出　　处：《CCS Chemistry》2023年第5期1077-1085,共9页中国化学会会刊（英文）

基　　金：the NSFC(grant nos.21871096,22071062,22271096),and the Fundamental Research Funds for the Central Universities,SCUT.

摘　　要：Conjugated polyene motifs are ubiquitous in various natural products and functional molecules;however,their synthesis is very challenging because of the required lengthy and time-consuming processes.We herein report an efficient approach for the synthesis of(E,E)-trienes via cationic rhodium catalysis using acetylene and simple alkenes bearing diverse directing groups as the starting materials.The reaction featured high step economy,excellent functional group compatibility,and exclusive stereoselectivity.Various directing groups such as carbonyl,sulfone,phosphate,hydroxyl,and amino were compatible.Furthermore,the triene products allowed versatile elaborations,providing rapid and convenient access to several important bioactive molecules,including vitamin A,(+)-roxaticin,and other complex polyenes.Mechanistic experiments showed that the directing group on the alkene played a crucial role in the reaction.

关 键 词：ACETYLENE rhodium catalysis linear trimerization (E E)-triene POLYENE 

分 类 号：O62[理学—有机化学]