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Redox-Active Reagents for Photocatalytic Generation of the OCF3 Radical and (Hetero)Aryl C-H Trifluoromethoxylation.


ABSTRACT: The trifluoromethoxy (OCF3 ) radical is of great importance in organic chemistry. Yet, the catalytic and selective generation of this radical at room temperature and pressure remains a longstanding challenge. Herein, the design and development of a redox-active cationic reagent (1) that enables the formation of the OCF3 radical in a controllable, selective, and catalytic fashion under visible-light photocatalytic conditions is reported. More importantly, the reagent allows catalytic, intermolecular C-H trifluoromethoxylation of a broad array of (hetero)arenes and biorelevant compounds. Experimental and computational studies suggest single electron transfer (SET) from excited photoredox catalysts to 1 resulting in exclusive liberation of the OCF3 radical. Addition of this radical to (hetero)arenes gives trifluoromethoxylated cyclohexadienyl radicals that are oxidized and deprotonated to afford the products of trifluoromethoxylation.

SUBMITTER: Zheng W 

PROVIDER: S-EPMC6278930 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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Redox-Active Reagents for Photocatalytic Generation of the OCF<sub>3</sub> Radical and (Hetero)Aryl C-H Trifluoromethoxylation.

Zheng Weijia W   Lee Johnny W JW   Morales-Rivera Cristian A CA   Liu Peng P   Ngai Ming-Yu MY  

Angewandte Chemie (International ed. in English) 20180920 42


The trifluoromethoxy (OCF<sub>3</sub> ) radical is of great importance in organic chemistry. Yet, the catalytic and selective generation of this radical at room temperature and pressure remains a longstanding challenge. Herein, the design and development of a redox-active cationic reagent (1) that enables the formation of the OCF<sub>3</sub> radical in a controllable, selective, and catalytic fashion under visible-light photocatalytic conditions is reported. More importantly, the reagent allows  ...[more]

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