Bismuth(III)-Catalyzed 1,8-Addition/Cyclization/Rearrangement of Propargylic para-Quinone Methides with 2‑Vinylphenol: Synthesis of Indeno[2,1‑c]chromenes

The unique reactivity of in situ generated propargylic para-quinone methides as a new type of five-carbon synthon has been discovered by a novel bismuth­(III)-catalyzed tandem annulation reaction. This 1,8-addition/cyclization/rearrangement cyclization cascade reaction is characterized by unusual st...

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Published in:Organic letters 2023-03, Vol.25 (8), p.1299-1304
Main Authors: Zhu, Zhi-Qiang, Wu, Teng-Fei, Pan, Han-Peng, Peng, Jin-Bao, Ma, Ai-Jun, Zhang, Xiang-Zhi
Format: Article
Language:English
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Summary:The unique reactivity of in situ generated propargylic para-quinone methides as a new type of five-carbon synthon has been discovered by a novel bismuth­(III)-catalyzed tandem annulation reaction. This 1,8-addition/cyclization/rearrangement cyclization cascade reaction is characterized by unusual structural reconstruction of 2-vinylphenol, involving cleavage of the C1′C2′ bond and formation of four new bonds. This method provides a convenient and mild approach to generate synthetically important functionalized indeno­[2,1-c]­chromenes. The mechanism of the reaction is proposed from several control experiments.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00179