铑催化芳甲酰乙腈与硫叶立德氧化环化合成多取代萘/2,3-二氢苯并色烯  

Rholdium-Catalyzed Cascade Oxidative Annulation of Benzoylacetonitriels by Sulfoxonium Ylides Leading to Substituted Naphthalenes/Benzo[de]Chromenes

作　　者：孙松[1] 徐圣博 SUN Song;XU Shengbo(School of Petrochemical Engineering,Changzhou University,Changzhou 213164,China)

机构地区：[1]常州大学石油化工学院,江苏常州213164

出　　处：《常州大学学报（自然科学版）》2019年第3期23-33,共11页Journal of Changzhou University：Natural Science Edition

基　　金：国家自然科学基金资助项目(20160129);江苏省自然科学基金资助项目(BK20150263)

摘　　要：研究了铑(III)催化芳甲酰乙腈与硫叶立德的[4+2]环化反应,合成了一系列的多取代萘甲腈,且该反应产率较高和官能团适应性好。该反应可能经历了连续的铑(III)插入碳-氢键、还原消除和环化反应。在此过程中,硫叶立德作为一种高效的卡宾前体。另外,当硫叶立德的用量提高到两倍物质的量时,所得产物主要是苯并色烯。Rh(III)-catalyzed [4+2]-annulation of benzoylacetonitriles with sulfoxonium ylides was developed to access substituted naphthalenes in moderate to excellent yields with good functional group compatibilities.This procedure proceeded with the sequential insertion of the Rh(III) carbene to the C-H bond,reductive elimination and cyclization steps,where sulfoxonium ylides served as an efficient and stable carbene precursor.Notably,benzo[ de ]chromenes were formed in the presence of two equivalents of sulfoxonium ylides.

关 键 词：铑催化 环化 芳甲酰乙腈 硫叶立德 多取代萘 苯并色烯 

分 类 号：O625.11[理学—有机化学]