Synthesis of Carbamoyl Azides from Redox-Active Esters and TMSN₃

Abstract

An efficient method for construction of C–N bonds is reported here. The iron-catalyzed azidation of N-hydroxy phthalimide (NHP) esters provides a convenient approach for the synthesis of carbamoyl azides with good substrate scope and functional group tolerance. Both aryl carbon C(sp²) and alkyl carbon C(sp³) sources can be used deliver the carbamoyl azides. Mechanistic studies were conducted and a two-stage process was identified.

Key words

redox-active esters - iron catalysis - NHP esters - azidation - carbamoyl azides

Publikationsverlauf

Eingereicht: 24. Februar 2023

Angenommen nach Revision: 06. Juni 2023

Accepted Manuscript online:
06. Juni 2023

Artikel online veröffentlicht:
21. Juli 2023

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• 15 Typical Procedure: A flame-dried reaction tube with a magnetic stirring bar was charged with NHP ester 1a (0.5 mmol, 133 mg), ferric acetate (10 mol%, 9.5 mg) and THF (5.0 mL) under a nitrogen atmosphere. TMSN₃ (1.5 mmol, 0.2 mL) was then injected into the tube and the mixture was heated at 70 °C (oil bath) for 24 h. After reaction completion as detected by TLC, the solid was removed by filtration and the filtrate was concentrated. The residue was purified by column chromatography (silica gel, PE/EtOAc = 10:1) to afford the carbamoyl azide 2a (73.7 mg, 91% yield) as a white solid; mp 105–106 °C. ¹H NMR (600 MHz, CDCl₃): δ = 7.42 (d, J = 8.1 Hz, 2 H), 7.35–7.31 (m, 2 H), 7.12 (t, J = 7.4 Hz, 1 H), 6.83 (br, 1 H). ¹³C NMR (151 MHz, CDCl₃): δ = 154.00, 136.95, 129.31, 124.75, 119.27.