2-Pyridone-Enhanced Mn-Catalysis for the Synthesis of ortho -Deuterated Aromatic Nitriles.

Autor:	Liu Y; NingboTech-Cuiying Joint Laboratory of Stable Isotope Technology, School of Biological and Chemical Engineering, NingboTech University, Ningbo 315100, People's Republic of China.; School of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, People's Republic of China., Qian T; NingboTech-Cuiying Joint Laboratory of Stable Isotope Technology, School of Biological and Chemical Engineering, NingboTech University, Ningbo 315100, People's Republic of China.; School of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, People's Republic of China., Bai JF; NingboTech-Cuiying Joint Laboratory of Stable Isotope Technology, School of Biological and Chemical Engineering, NingboTech University, Ningbo 315100, People's Republic of China., Zheng J; NingboTech-Cuiying Joint Laboratory of Stable Isotope Technology, School of Biological and Chemical Engineering, NingboTech University, Ningbo 315100, People's Republic of China.; School of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, People's Republic of China., Zhou Y; NingboTech-Cuiying Joint Laboratory of Stable Isotope Technology, School of Biological and Chemical Engineering, NingboTech University, Ningbo 315100, People's Republic of China., Jiang ZJ; NingboTech-Cuiying Joint Laboratory of Stable Isotope Technology, School of Biological and Chemical Engineering, NingboTech University, Ningbo 315100, People's Republic of China., Chen J; NingboTech-Cuiying Joint Laboratory of Stable Isotope Technology, School of Biological and Chemical Engineering, NingboTech University, Ningbo 315100, People's Republic of China., Gao Z; NingboTech-Cuiying Joint Laboratory of Stable Isotope Technology, School of Biological and Chemical Engineering, NingboTech University, Ningbo 315100, People's Republic of China.; Ningbo Cuiying Chemical Technology Co. Ltd., Ningbo 315100, People's Republic of China.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2024 Nov 29; Vol. 26 (47), pp. 10170-10175. Date of Electronic Publication: 2024 Nov 15.
DOI:	10.1021/acs.orglett.4c04061
Abstrakt:	We herein present a method for the synthesis of ortho -deuterated aryl nitrile using Mn(CO) 5 Br as catalyst with CH 3 OD 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.
Databáze:	MEDLINE
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