Decarbonylative Sonogashira cross-coupling:a fruitful marriage of alkynes with carboxylic acid electrophiles  

作　　者：Chengwei Liu Michal Szostak 

机构地区：[1]School of Chemical Engineering and Technology,Yantai Nanshan University,Longkou,Yantai,Shandong 265713,China [2]School of Chemistry and Materials Science,Nanjing University of Information Science and Technology,219 Ningliu Road,Nanjing,Jiangsu 210044,China [3]Department of Chemistry,Rutgers University,73 Warren Street,Newark,NJ 07102,USA

出　　处：《Organic Chemistry Frontiers》2022年第1期216-222,共7页有机化学前沿（英文）

基　　金：Yantai Nanshan University,Nanjing University of Information Science and Technology,the NIH(1R35GM133326);the NSF(CAREER CHE-1650766);Rutgers University for generous support.

摘　　要：The Sonogashira cross-coupling is one of the most fundamental C–C bond-forming reactions,wherein the strategic value of an alkyne moiety has found widespread applications at the frontiers of organic chemistry,materials science and drug discovery as the cornerstone building block of chemical synthesis.Although traditional variants of Sonogashira cross-coupling involve aryl halides and pseudohalides as electrophiles,recently,tremendous advances have been made in the unconventional disconnection exploiting common carboxylic acids by a decarbonylation/transmetalation pathway.This manifold(1)permits one to take advantage of carboxylic acids as a ubiquitous class of substrates in organic synthesis that are derived from an orthogonal pool of precursors to aryl halides and pseudohalides and(2)combines the benefits of the palladium-catalyzed C(sp^(2))–C(sp)coupling of terminal alkynes with the inherent presence of the carboxylic acid moiety in pharmaceuticals,natural products and organic materials.In this highlight article,we summarize the recent progress in the decarbonylative Sonogashira cross-coupling of carboxylic acid electrophiles to produce arylalkynes and conjugated enynes as a novel avenue for chemical synthesis,whereby a large number of chemical reactions critically rely on transformations of alkynes.

关 键 词：coupling CARBONYL MOIETY 

分 类 号：O62[理学—有机化学]