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Rhodium(III)-Catalyzed C-H Activation: An Oxidative Intramolecular Heck-Type Reaction Directed by a Carboxylic Acid.

ABSTRACT: Carboxylic acids effectively direct C-H activation for Rhodium(III)-catalyzed intramolecular Heck-type reactions. A catalytic amount of Cu(OAc)2 is used as the external oxidant with oxygen likely acting as the terminal oxidant. Additionally, a novel electron-deficient RhIII catalyst was found to be more effective that [RhCp*Cl2]2 with some substrates. A wide variety of complex dihydrobenzofurans, dihydrobenzopyrans, and other bicycles that can be easily further functionalized are now accessible through relatively mild reaction conditions.

SUBMITTER: Davis TA 

PROVIDER: S-EPMC4986923 | biostudies-literature | 2015 Jul

REPOSITORIES: biostudies-literature

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Rhodium(III)-Catalyzed C-H Activation: An Oxidative Intramolecular Heck-Type Reaction Directed by a Carboxylic Acid.

Davis Tyler A TA   Wang Chuanqi C   Rovis Tomislav T  

Synlett : accounts and rapid communications in synthetic organic chemistry 20150615 11

Carboxylic acids effectively direct C-H activation for Rhodium(III)-catalyzed intramolecular Heck-type reactions. A catalytic amount of Cu(OAc)<sub>2</sub> is used as the external oxidant with oxygen likely acting as the terminal oxidant. Additionally, a novel electron-deficient Rh<sup>III</sup> catalyst was found to be more effective that [RhCp*Cl<sub>2</sub>]<sub>2</sub> with some substrates. A wide variety of complex dihydrobenzofurans, dihydrobenzopyrans, and other bicycles that can be easil  ...[more]

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