Organic Letters
Organic Letters
5 years ago

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

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
Luo Yang, Saihong Wan, Yuanyuan Jia, Qijian Jiang, Xiaodong Si, Guiyu Guo, Wang Zhou
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. 13C 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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02052

DOI: 10.1021/acs.orglett.7b02052

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