Ir(iii)/Ag(i)-catalyzed directly C–H amidation of arenes with OH-free hydroxyamides as amidating agents
Youpeng Zuo, Meijun Liu, Jun Du, Tianren Zhang, Xiaoqing Wang, Cong Wang
TL;DR
This paper presents a new method for efficiently creating C–H amides using OH-free hydroxyamides without needing extra oxidants.
Contribution
The use of OH-free hydroxyamides as amidating agents in Ir(iii)-catalyzed C–H amidation is novel and efficient.
Findings
The reaction works with various functional groups and does not require external oxidants.
A wide range of OH-free hydroxyamides, including non-conjugated ones, can be used effectively.
The method produces N-(2-(1H-pyrazol-1-yl)alkyl)amide derivatives in good to excellent yields.
Abstract
A versatile Ir(iii)-catalyzed C–H amidation of arenes by employing readily available and stable OH-free hydroxyamides as a novel amidation source. The reaction occurred with high efficiency and tolerance of a range of functional groups. A wide scope of aryl OH-free hydroxyzamides, including conjugated and challenging non-conjugated OH-free hydroxyzamides, were capable of this transformation and no addition of an external oxidant is required. This protocol provided a simple, straightforward and economic method to a variety N-(2-(1H-pyrazol-1-yl)alkyl)amide derivates with good to excellent yield. Mechanistic study demonstrated that reversible C–H bond functionalisation might be involved in this reaction. A versatile Ir(iii)-catalyzed C–H amidation of arenes by employing readily available and stable OH-free hydroxyamides as a novel amidation source.
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Taxonomy
TopicsCatalytic C–H Functionalization Methods · Synthesis and Catalytic Reactions · Catalytic Cross-Coupling Reactions