Intramolecular rhodium carbenoid insertions into aromatic C—H bonds. Preparation of 1,3-dihydrothiophene 2,2-dioxides fused onto aromatic rings

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Abstract

The preparation of 1-carboalkoxy-1,3-dihydrobenzo[b]thiophene 2,2-dioxides via rhodium acetate or rhodium trifiuoro-acetate catalyzed decomposition of α-diazo-β-arylmethanesulfonyl esters is described. The reaction has been extended to yield 1,3-dihydrothiophene 2,2-dioxides fused to the 2,3 position of thiophene and indole, but not of furans. In the latter case products derived from the opening of the furan ring were obtained. Keywords: synthesis, 1-carboalkoxy-1,3-dihydrobenzo[b]thiophene 2,2-dioxides, intramolecular carbenoid insertions, rhodium acetate catalysis.

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