2-Pyridone-Enhanced Mn-Catalysis for the Synthesis of ortho-Deuterated Aromatic Nitriles
Yanran Liu1,2, Tao Qian1,2, Jian-Fei Bai1
1NingboTech-Cuiying Joint Laboratory of Stable Isotope Technology, School of Biological and Chemical Engineering, NingboTech University, Ningbo 315100, People's Republic of China.
Abstract:
We herein present a method for the synthesis of ortho-deuterated aryl nitrile using Mn(CO)5Br as catalyst with CH3OD as deuteratium source, where the structure of aryl imidates is used for interconversion with a cyanide group. This method features a broad substrate range and excellent functional group tolerance, allowing late modification of various complex molecules with good yields and deuterium incorporation. Mechanistic studies suggest that 2-pyridone is crucial to the success of this chemistry, serving as an endogenous base that enhances the rate of hydrogen isotope exchange.
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