Unknown

Dataset Information

0

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

altmetric image

Publications

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]

Similar Datasets

| S-EPMC7308607 | biostudies-literature
| S-EPMC7702167 | biostudies-literature
| S-EPMC6429774 | biostudies-literature
| S-EPMC7244481 | biostudies-literature
| S-EPMC8457207 | biostudies-literature
| S-EPMC3310175 | biostudies-literature
| S-EPMC4909548 | biostudies-literature
| S-EPMC6790943 | biostudies-literature
| S-EPMC4668583 | biostudies-literature
| S-EPMC5685551 | biostudies-literature