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Catalytic C-H Trifluoromethoxylation of Arenes and Heteroarenes.


ABSTRACT: The intermolecular C-H trifluoromethoxylation of arenes remains a long-standing and unsolved problem in organic synthesis. Herein, we report the first catalytic protocol employing a novel trifluoromethoxylating reagent and redox-active catalysts for the direct (hetero)aryl C-H trifluoromethoxylation. Our approach is operationally simple, proceeds at room temperature, uses easy-to-handle reagents, requires only 0.03?mol?% of redox-active catalysts, does not need specialized reaction apparatus, and tolerates a wide variety of functional groups and complex structures such as sugars and natural product derivatives. Importantly, both ground-state and photoexcited redox-active catalysts are effective. Detailed computational and experimental studies suggest a unique reaction pathway where photoexcitation of the trifluoromethoxylating reagent releases the OCF3 radical that is trapped by (hetero)arenes. The resulting cyclohexadienyl radicals are oxidized by redox-active catalysts and deprotonated to form the desired products of trifluoromethoxylation.

SUBMITTER: Zheng W 

PROVIDER: S-EPMC6105550 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Catalytic C-H Trifluoromethoxylation of Arenes and Heteroarenes.

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

Angewandte Chemie (International ed. in English) 20180313 31


The intermolecular C-H trifluoromethoxylation of arenes remains a long-standing and unsolved problem in organic synthesis. Herein, we report the first catalytic protocol employing a novel trifluoromethoxylating reagent and redox-active catalysts for the direct (hetero)aryl C-H trifluoromethoxylation. Our approach is operationally simple, proceeds at room temperature, uses easy-to-handle reagents, requires only 0.03 mol % of redox-active catalysts, does not need specialized reaction apparatus, an  ...[more]

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