Discovery of 2-(pyridin-2-yl)aniline as a directing group for the sp2 C-H bond amination mediated by cupric acetate.

doi:10.1039/c7ob01353a

Paper

Discovery of 2-(pyridin-2-yl)aniline as a directing group for the sp2 C-H bond amination mediated by cupric acetate.

Published Aug 9, 2017 · Hong-Yi Zhao, Hui-Yan Wang, Shuai Mao

Organic & biomolecular chemistry

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Abstract

2-(Pyridin-2-yl) aniline was designed as a new, removable directing group in promoting C-H amination mediated by cupric acetate. Employing this auxiliary, the β-C(sp2)-H bonds of benzamide derivatives can be effectively aminated with a variety of amines in moderate to good yields with good functional group tolerance in air. In addition, the quinazolinone derivatives were isolated from the reaction mixture of N-(2-(pyridin-2-yl)phenyl)benzamide with formamide or 5-nitroindole. The corresponding mechanism is discussed. These results indicate that 2-(pyridine-2-yl)aniline can serve as a directing group.

Study Snapshot

2-(pyridin-2-yl) aniline effectively promotes C-H amination mediated by cupric acetate, resulting in moderate to good yields and good functional group tolerance in air.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Discovery of 2-(pyridin-2-yl)aniline as a directing group for the sp2 C-H bond amination mediated by cupric acetate.

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Citations

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A modular iridium catalyst enables highly enantioselective and site-selective catalytic borylation of remote C(sp3)-H bonds in aliphatic amides and esters, offering versatile synthetic utility.

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