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

doi:10.1002/cjoc.202400874

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (2) : 199 -204. DOI: 10.1002/cjoc.202400874

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

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Abstract

Comprehensive 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.

Keywords

Hetero-allenes / 2-Pyrones / Diels–Alder reaction / Claisen rearrangement / Decarboxylation / Tandem reaction

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Bin Chen, Shan Zhong, Huilin Zhan, Zhangyu Han, Jianwei Sun, Hai Huang. Ytterbium-Catalyzed Tandem Diels–Alder/Claisen Rearrangement/Decarboxylation of Hetero-Allenes for the Synthesis of Diarylmethanes. Chinese Journal of Chemistry, 2025, 43(2): 199-204 DOI:10.1002/cjoc.202400874