Extension of Highly Efficient Alcohol-promoted Rearrangement into One-pot Domino Palladium-catalyzed Carbonylation for Sterically Crowded Aromatic Six-membered Imides
作者机构：Advanced Innovation Center for Soft Matter Science and EngineeringState Key Laboratory of Organic-Inorganic CompositesBeijing University of Chemical TechnologyBeijing 100029P.R.China State Key Laboratory of Catalytic Materials and Reaction EngineeringResearch Institute of Petroleum ProcessingSINOPECBeijing 100083P.R.China National Demonstration Center for Experimental Life Sciences&Biotechnology EducationBeijing Normal University100875 BeijingP.R.China Wuhan National Laboratory for OptoelectronicsHuazhong University of Science and TechnologyWuhan 430074P.R.China State Key Laboratory of Optoelectronic Materials and TechnologiesSun Yat-sen UniversityGuangzhou 510275P.R.China State Key Laboratory of Fine ChemicalsDalian University of TechnologyDalian 116024P.R.China
出 版 物：《Chemical Research in Chinese Universities》 (高等学校化学研究（英文版）)
年 卷 期：2023年第39卷第6期
页 面：1106-1110页
核心收录：
学科分类：07[理学] 070303[理学-有机化学] 0703[理学-化学]
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.
主 题：Bulky aromatic imide Imide isomerization Domino synthesis Organic semiconductor
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.
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