Journal
CHEM
Volume 2, Issue 3, Pages 383-392Publisher
CELL PRESS
DOI: 10.1016/j.chempr.2017.02.006
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Funding
- Exploratory Research for Advanced Technology (ERATO) program from the Japan Science and Technology Agency (JST)
- Japan Society for the Promotion of Science (JSPS) [JP26888007]
- Takeda Pharmaceutical Company Award in Synthetic Organic Chemistry
- Sumitomo Foundation
- World Premier International Research Center (WPI) Initiative
- Grants-in-Aid for Scientific Research [15K17821] Funding Source: KAKEN
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In light of the importance of arylamine derivatives in organic materials, pharmaceuticals, and agrochemicals, the development of efficient aromatic C-H amination has long been sought after. Although many attempts have been made to achieve dehydrogenative C-H amination, the low reactivity of simple arenes renders equimolar coupling with amine derivatives a formidable task in synthetic chemistry. Herein, we report equimolar C-H/N-H coupling of arenes and sulfonimides through dehydrogenative aromatic imidation. Thiswas accomplished by means of a ruthenium-based photoredox mediator that employed the arene as the limiting reagent. A wide range of arenes, such as polycyclic aromatic hydrocarbons and heteroarenes, as well as a variety of sulfonimides, were applicable to the reaction. This electrochemistry-based mechanistic study has uncovered that the coupling reaction is initiated by the oxidation of sulfonimides by the ruthenium catalyst.
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