Tetrabutylammonium iodide-catalyzed oxidative α-azidation of β-ketocarbonyl compounds using sodium azide

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 1510 - 1517

Published: July 5, 2024

We herein report the oxidative α-azidation of carbonyl compounds by using NaN 3 in presence dibenzoyl peroxide catalyzed tetrabutylammonium iodide (TBAI). By utilizing these readily available bulk chemicals a variety cyclic β-ketocarbonyl derivatives can be efficiently α-azidated under operationally simple conditions. Control experiments support mechanistic scenario involving situ formation an ammonium hypoiodite species which first facilitates α-iodination pronucleophile, followed phase-transfer-catalyzed nucleophilic substitution azide. Furthermore, we also show that analogous α-nitration NaNO 2 otherwise identical conditions is possible as well.

Language: Английский

Syntheses of diarylmethanes via an oxidative benzylic functionalization of p‐alkyl phenol derivatives under quaternary ammonium hypoiodite catalysis

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 26, 2024

We herein report two strategies for the quaternary ammonium hypoiodite-mediated oxidative benzylic functionalization of p-alkyl phenol derivatives. By using either dibenzoylperoxide or H

Language: Английский