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Rh(iii)-Catalyzed sequential ortho-C–H oxidative arylation/cyclization of sulfoxonium ylides with quinones toward 2-hydroxy-dibenzo[b,d]pyran-6-ones

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Abstract

A rhodium(III)-catalyzed ortho-C–H functionalization of sulfoxonium ylides followed by intramolecular annulation reactions with quinones was described, where the carbonyl in sulfoxonium ylides served as a chelation group. This protocol leads to the efficient formation of 2-hydroxy-6H-benzo[c]chromen-6-one derivatives, proceeding with the cleavage of the C(O)–S bond in sulfoxonium ylides. This protocol featured high chemo-selectivity and functional group tolerance, where sulfoxonium ylides acted as the aroyl sources.

Graphical abstract: Rh(iii)-Catalyzed sequential ortho-C–H oxidative arylation/cyclization of sulfoxonium ylides with quinones toward 2-hydroxy-dibenzo[b,d]pyran-6-ones

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Article information


Submitted
08 Jan 2020
Accepted
07 May 2020
First published
07 May 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Rh(III)-Catalyzed sequential ortho-C–H oxidative arylation/cyclization of sulfoxonium ylides with quinones toward 2-hydroxy-dibenzo[b,d]pyran-6-ones

Y. Dong, J. Yu, S. Sun and J. Cheng, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC00176G

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