t-BuOK促进的还原脱砜/脱氢反应:选择性合成2-取代的1,3-共轭二烯及其应用  

t-BuOK-Mediated Reductive Desulfonylation/Dehydrogenation for the Synthesis of 2-Substituted 1,3-Dienes and Their [4+2] Cycloaddition Reactions

作　　者：孙佳兵 苗涛[1] 李品华[1] 王磊[1,2,3] Sun Jiabing;Miao Tao;Li Pinhua;Wang Lei(Key Laboratory of Green and Precise Synthetic Chemistry and Applications,Ministry of Education,School of Chemistty and Materials Science,Huaibei Normal University,Huabei,Anhui 235000;Advanced Research Institute and Department of Chemistry,Taizhou University,Taizhou,Zhejiang 318000;State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032)

机构地区：[1]淮北师范大学化学与材料科学学院绿色和精准合成化学及应用教育部重点实验室,安徽淮北235000 [2]台州学院医药化工与材料工程学院,浙江台州318000 [3]中国科学院上海有机化学研究所金属有机化学国家重点实验室,上海200032

出　　处：《有机化学》2021年第8期3144-3156,共13页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.21772062,22071171,21602072);安徽省高校自然科学基金(No.KJ2019ZD66)资助项目.

摘　　要：发展了一种叔丁醇钾促进的(Z)-C6-乙烯基砜基菲啶的脱砜、脱氢串联反应,用于选择性地合成1,3-共轭二烯.该反应无需过渡金属催化剂,底物适用范围广,以良好的收率得到相应的目标产物,为菲啶官能化的1,3-共轭二烯的合成提供了新颖和有效的方法.此外,通过与富马腈的[4+2]环加成反应,实现了1,3-共轭二烯的合成应用.A t-BuOK-mediated desulfonylation/dehydrogenation cascade reaction of(Z)-C6-(vinyl sulfone)phenanthridines is described. This process provides a novel and efficient strategy for the synthesis of 1,3-dienes with phenanthridinyl units in good yields under transition-metal-free conditions. Furthermore, the application of the generated 1,3-dienes in the [4+2] cycloaddition has been demonstrated by reacting with dienophiles such as fumaronitrile in a two-step procedure.

关 键 词：叔丁醇钾 脱砜反应 1 3-共轭二烯 环加成反应 

分 类 号：O623.122[理学—有机化学]