Ytterbium-Catalyzed Tandem Diels-Alder/Claisen Rearrangement/Decarboxylation of Hetero-Allenes for the Synthesis of Diarylmethanes  

作　　者：Bin Chen Shan Zhong Huilin Zhan Zhangyu Han Jianwei Sun Hai Huang 

机构地区：[1]Jiangsu Key Laboratory of Advanced Catalytic Materials&Technology,School of Petrochemical Engineering,Changzhou University,Changzhou,Jiangsu,213164 China [2]Department of Chemistry,The Hong Kong University of Science and Technology,Clear Water Bay,Kowloon,Hong Kong,SAR,999077 China

出　　处：《Chinese Journal of Chemistry》2025年第2期199-204,共6页中国化学(英文版)

基　　金：supported by the NSFC(22071210,22101033,22201023,22271242);the Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology(BM2012110);the Natural Science Foundation of Jiangsu Province(BK20210849);the Innovation&Entrepreneurship Talents Plan of Jiangsu Province(JSSCRC2021536).

摘　　要：A tandem Diels–Alder reaction/Claisen rearrangement/decarboxylation strategy of N-allenamides (or aryloxyallenes) with 3-alkoxycarbonyl-2-pyrones has been developed for the efficient synthesis of diarylmethanes with moderate to good yields. The reaction exhibits good functional group tolerance and can be applied to late-stage modifications of known drug molecules. Mechanistic studies indicate that the ester group at the 3-position of 2-pyrones is essential, and the initial Diels–Alder reaction between the 2-pyrones and the proximal C=C bond of the N-allenamides (or aryloxyallenes) is crucial for the success of the reaction.

关 键 词：Hetero-allenes 2-Pyrones Diels-Alder reaction Claisen rearrangement DECARBOXYLATION Tandem reaction 

分 类 号：O62[理学—有机化学]