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Copper-catalyzed C-H azidation of anilines under mild conditions.

Journal of the American Chemical Society (2012-11-08)
Conghui Tang, Ning Jiao
ABSTRACT

A novel and efficient copper-catalyzed azidation reaction of anilines via C-H activation has been developed. This method, in which the primary amine acts as a directing group by coordinating to the metal center, provides ortho azidation products regioselectively under mild conditions. This effective route for the synthesis of aryl azides is of great significance in view of the versatile reactivity of the azide products.

MATERIALS
Product Number
Brand
Product Description

Supelco
Aniline, analytical standard
Sigma-Aldrich
Aniline, ACS reagent, ≥99.5%
Sigma-Aldrich
Aniline-15N, 98 atom % 15N
Sigma-Aldrich
Aniline, ReagentPlus®, 99%
Supelco
Aniline solution, certified reference material, 5000 μg/mL in methanol
Sigma-Aldrich
Aniline hydrochloride, ≥99%