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Practical synthesis of isocoumarins via Rh(III)-catalyzed C-H activation/annulation cascade.

ABSTRACT: Herein, we report an unprecedented Rh(III)-catalyzed C-H activation/annulation cascade of readily available enaminones with iodonium ylides towards the convenient synthesis of isocoumarins. This coupling system proceeds in useful chemical yields (up to 93%) via a cascade C-H activation, Rh-carbenoid migratory insertion and acid-promoted intramolecular annulation. The success of gram-scale reaction and diverse functionalization of isocoumarins demonstrated the synthetic utility of this protocol.

SUBMITTER: Gao QC 

PROVIDER: S-EPMC9907013 | biostudies-literature | 2023

REPOSITORIES: biostudies-literature

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Practical synthesis of isocoumarins via Rh(III)-catalyzed C-H activation/annulation cascade.

Gao Qian-Ci QC   Li Yi-Fei YF   Xuan Jun J   Hu Xiao-Qiang XQ  

Beilstein journal of organic chemistry 20230130

Herein, we report an unprecedented Rh(III)-catalyzed C-H activation/annulation cascade of readily available enaminones with iodonium ylides towards the convenient synthesis of isocoumarins. This coupling system proceeds in useful chemical yields (up to 93%) via a cascade C-H activation, Rh-carbenoid migratory insertion and acid-promoted intramolecular annulation. The success of gram-scale reaction and diverse functionalization of isocoumarins demonstrated the synthetic utility of this protocol. ...[more]

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