Acylation of Arylamines with Triethylamine Derivatives in Combination with tert‐Butyl Hydroperoxide

Abstract

N-acylation of arylamines with di-and trialkyl amines has been reported. This approach provides a general synthesis of aromatic amides by an alkyl transfer through cleavage of the CÀ N bond, and acts as a model for N-dealkylations and N-acylations. Additionally, the synthesis is a promising method towards amidation reactions, wherein di-and trialkyl amine derivatives are employed as sources of acyl carbon atoms and tert-butyl hydroperoxide is employed as the oxygen source of the acyl group.

Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses

“…It was then subjected to silica gel column chromatography ( n -hexane/CH 2 Cl 2 , v/v = 1:2) to afford 5a as a yellow solid in 50% yield (0.75 g, 5.0 mmol). 1 H and 13 C NMR spectra are in agreement with those reported in the literature …”

“…1 H and 13 C NMR spectra are in agreement with those reported in the literature. 43 1 H NMR (400 MHz, CDCl 3 , 293 K): δ 7.52 (d, J = 8.0 Hz, 2H), 7.32 (t, J = 7.6 Hz, 2H), 7.10 (t, J = 7.2 Hz, 1H), 2.43 (q, J = 7.6 Hz, 2H), 1.26 (t, J = 7.6 Hz, 3H). 13 C{ 1 H} NMR (100 MHz, CDCl 3 , 293 K): δ 171.9, 137.9, 129.0, 124.2, 119.7, 30.8, 9.7.…”

Palladium-Catalyzed Multistep Tandem Carbonylation/N-Dealkylation/Carbonylation Reaction: Access to Isatoic Anhydrides

“…Tertiary anilines are valuable commodity chemicals and useful core structures for agrochemicals, pharmaceutical ingredients, and functional materials . As a typical example, tertiary anilines have also been utilized in C–N bond cleavage transformations . However, most C–N bond activation of tertiary anilines has focused on the cross-coupling of the Csp 2 –N bond with organometallic reagents .…”