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

doi:10.1007/s40242-023-3209-8

Chemical Research in Chinese Universities ›› 2023, Vol. 39 ›› Issue (6): 1106-1110.doi: 10.1007/s40242-023-3209-8

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

GUO Rong^1,2, ZHANG Jingmei^1,4,5, JIA Xiaohui³, SHI Chunfeng², QIE Fengxiang², and ZHEN Yonggang^1,6

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

Received:2023-09-09 Online:2023-12-01 Published:2023-11-18
Contact: JIA Xiaohui, QIE Fengxiang, ZHEN Yonggang E-mail:xhjia@bnu.edu.cn;qiefengxiang.ripp@sinopec.com;zhenyg@buct.edu.cn
Supported by:
This work was 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) and the Fund of the State Key Laboratory of Optoelectronic Materials and Technologies (Sun Yat-sen University), China.

Abstract

Abstract: 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 ¹H 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.

Key words: Bulky aromatic imide, Imide isomerization, Domino synthesis, Organic semiconductor

GUO Rong, ZHANG Jingmei, JIA Xiaohui, SHI Chunfeng, QIE Fengxiang, and ZHEN Yonggang. Extension of Highly Efficient Alcohol-promoted Rearrangement into One-pot Domino Palladium-catalyzed Carbonylation for Sterically Crowded Aromatic Six-membered Imides[J]. Chemical Research in Chinese Universities, 2023, 39(6): 1106-1110.

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

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