Extension of Highly Efficient Alcohol-promoted Rearrangement into One-pot Domino Palladium-catalyzed Carbonylation for Sterically Crowded Aromatic Six-membered Imides  

作　　者：GUO Rong ZHANG Jingmei JIA Xiaohui SHI Chunfeng QIE Fengxiang ZHEN Yonggang 

机构地区：[1]Advanced Innovation Center for Soft Matter Science and Engineering,State Key Laboratory of Organic-Inorganic Composites,Beijing University of Chemical Technology,Beijing 100029,P.R.China [2]State Key Laboratory of Catalytic Materials and Reaction Engineering,Research Institute of Petroleum Processing,SINOPEC,Beijing 100083,P.R.China [3]National Demonstration Center for Experimental Life Sciences&Biotechnology Education,Beijing Normal University,100875 Beijing,P.R.China [4]Wuhan National Laboratory for Optoelectronics,Huazhong University of Science and Technology,Wuhan 430074,P.R.China [5]State Key Laboratory of Optoelectronic Materials and Technologies,Sun Yat-sen University,Guangzhou 510275,P.R.China [6]State Key Laboratory of Fine Chemicals,Dalian University of Technology,Dalian 116024,P.R.China

出　　处：《Chemical Research in Chinese Universities》2023年第6期1106-1110,共5页高等学校化学研究（英文版）

基　　金：supported by the Fundamental Research Funds for the Central Universities,China(No.buctrc202103);the National Natural Science Foundation of China(Nos.21975263,22171019);the Project of the SINOPEC(No.222131);the Open Project Programs of Wuhan National Laboratory for Optoelectronics,China(No.2021WNLOKF005);the Fund of the State Key Laboratory of Fine Chemicals(Dalian University of Technology),China(No.KF2201);the Fund of the State Key Laboratory of Optoelectronic Materials and Technologies(Sun Yat-sen University),China.

摘　　要：Aromatic six-membered imides suffer the introduction of bulky substituents at the imide positions due to the formation of isoimides and low reactivity,preventing from the investigation of the intrinsic molecular properties.Here,we found a highly efficient alcohol-promoted rearrangement from isonaphthalimide to naphthalimide under acid or basic nonaqueous conditions,which can be regarded as model compounds for aromatic six-membered imides.We proposed two-step nucleophilic substitutions in the isomerization mechanistic pathways that were verified by the separation of a key intermediate.Furthermore,in-situ ^(1)H NMR exhibited the first-order kinetics for the isoimide loss process.Finally,the alcohol-promoted isoimide-imide rearrangement was extended to a palladium-catalyzed one-pot domino carbonylation reaction toward sterically crowded aromatic six-membered imides.

关 键 词：Bulky aromatic imide Imide isomerization Domino synthesis Organic semiconductor 

分 类 号：O62[理学—有机化学]