From Simple to Complex: Rhodium(III)-Catalyzed C-C Bond Cleavage and C-H Bond Functionalization for the Synthesis of 3a,8b-Dihydro-1H-cyclopenta[b]benzofuran-1-ones

A rhodium(III)-catalyzed strategy for the one-step synthesis of polysubstituted cis-3a,8b-dihydro-1H-cyclopenta[b]benzofuran-1-ones from simple 2'-hydroxychalcones and alkynes is developed. This novel transformation involves a sequential C-C bond cleavage and dehydrogenative annulation, leading...

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Bibliographic Details
Published in:Organic letters 2017-10, Vol.19 (19), p.5026-5029
Main Authors: Guo, Guiyu, Wan, Saihong, Si, Xiaodong, Jiang, Qijian, Jia, Yuanyuan, Yang, Luo, Zhou, Wang
Format: Article
Language:English
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Summary:A rhodium(III)-catalyzed strategy for the one-step synthesis of polysubstituted cis-3a,8b-dihydro-1H-cyclopenta[b]benzofuran-1-ones from simple 2'-hydroxychalcones and alkynes is developed. This novel transformation involves a sequential C-C bond cleavage and dehydrogenative annulation, leading to the product bearing a quaternary and a tertiary carbon center. C labeling experiments revealed that C-C bond cleavage takes place not only at the C-C(C═O) bond but also at the C≡C bond. This study provides an alternative strategy using C-C bond cleavage thus demonstrating the power of this strategy combined with C-H bond functionalization for assembling complex structures from simple starting materials.
ISSN:1523-7052
DOI:10.1021/acs.orglett.7b02052