Concise Report
Ytterbium-Catalyzed Tandem Diels–Alder/Claisen Rearrangement/Decarboxylation of Hetero-Allenes for the Synthesis of Diarylmethanes
Bin Chen,
Shan Zhong,
Huilin Zhan,
Zhangyu Han,
Jianwei Sun,
Hai Huang,
Bin Chen
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorShan Zhong
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorHuilin Zhan
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorZhangyu Han
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorJianwei Sun
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, SAR, 999077 China
Search for more papers by this authorCorresponding Author
Hai Huang
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu, 213164 China
E-mail: [email protected]Search for more papers by this authorBin Chen,
Shan Zhong,
Huilin Zhan,
Zhangyu Han,
Jianwei Sun,
Hai Huang,
Bin Chen
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorShan Zhong
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorHuilin Zhan
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorZhangyu Han
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu, 213164 China
Search for more papers by this authorJianwei Sun
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, SAR, 999077 China
Search for more papers by this authorCorresponding Author
Hai Huang
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu, 213164 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
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.
Supporting Information
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Appendix S1: Supporting Information |
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