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Synlett 2018; 29(16): 2191-2194
DOI: 10.1055/s-0037-1610653
DOI: 10.1055/s-0037-1610653
letter
Pd-Catalyzed Oxidation of Aldimines to Amides
This research is sponsored by research funds of Ningbo University (No. ZX2016000748) and the K. C. Wong Magna Fund in Ningbo University.Further Information
Publication History
Received: 19 June 2018
Accepted after revision: 17 July 2018
Publication Date:
21 August 2018 (online)
Abstract
Methods for the synthesis of amides via the direct oxidation of imines are rarely reported. Here we report an efficient method for Pd-catalyzed oxidation of imines to amide derivatives by the use of cheap aqueous tert-butyl hydroperoxide as an oxidant through a Wacker-type reaction. This method is practically convenient and displays high functional group tolerance, allowing a variety of imines to transform into the corresponding amide derivatives in moderate to good yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610653.
- Supporting Information
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- 16 Typical Procedure for the Preparation of N-Phenylbenzamide (2a) Pd(OAc)2 (0.01 mmol), N,1-diphenylmethanimine (1a, 0.2 mmol), TBHP (70 % solution in H2O, 6.0 equiv, 1.2 mmol), and DCE (1.5 mL) were added to a vial. The reaction mixture was stirred under 120 °C for 5 h. After that time, the reaction mixture was quenched with saturated Na2SO3 solution (consumption of residual TBHP) and extracted with EtOAc. The organic layer was separated and dried with Na2SO4. Removal of solvent followed by flash column chromatographic purification (EtOAc/PE) afforded N-phenylbenzamide (2a) as a white solid (33.5 mg, yield 85%). 1H NMR (400 MHz, CDCl3): δ = 7.94 (br s, 1 H), 7.86 (d, J = 7.3 Hz, 2 H), 7.65 (d, J = 7.9 Hz, 2 H), 7.54 (t, J = 7.3 Hz, 1 H), 7.47 (t, J = 7.4 Hz, 2 H), 7.36 (t, J = 7.8 Hz, 2 H), 7.15 (t, J = 7.4 Hz, 1 H) ppm. 13C NMR (101 MHz, CDCl3): δ = 165.7, 137.9, 135.0, 131.9, 129.1, 128.8, 127.0, 124.6, 120.2 ppm.