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Palladium-Catalyzed Remote meta-C-H Bond Deuteration of Arenes Using a Pyridine Template.

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Palladium-catalyzed meta-selective C-H deuteration of a series of substrates, including phenylacetic acids, hydrocinnamic acid, benzylphosphonate, benzylsulfonate, and benzyl and phenyl ethyl alcohol ester, is developed by using a pyridine-based directing… Click to show full abstract

Palladium-catalyzed meta-selective C-H deuteration of a series of substrates, including phenylacetic acids, hydrocinnamic acid, benzylphosphonate, benzylsulfonate, and benzyl and phenyl ethyl alcohol ester, is developed by using a pyridine-based directing template. The template is installed into the substrate through a practical ester linkage. Under mild reaction conditions, a variety of phenylacetic acids containing alkyl, methoxyl, and halo substituents are compatible in the reaction, resulting in high levels of D-incorporation at the meta position.

Keywords: using pyridine; deuteration; template; catalyzed remote; palladium catalyzed; meta

Journal Title: Organic letters
Year Published: 2019

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