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Synlett 2015; 26(13): 1862-1866
DOI: 10.1055/s-0034-1380811
DOI: 10.1055/s-0034-1380811
letter
tert-Butyl Peroxybenzoate Mediated Selective and Mild N-Benzoylation of Ammonia/Amines under Catalyst- and Solvent-Free Conditions
Autoren
Weitere Informationen
Publikationsverlauf
Received: 31. März 2015
Accepted after revision: 21. April 2015
Publikationsdatum:
08. Juni 2015 (online)
Abstract
A new protocol for the synthesis of amides from tert-butyl peroxybenzoate (TBPB) and ammonia/amines has been developed under catalyst- and solvent-free conditions. The ammonia, primary and secondary amines reacted smoothly with TBPB to furnish the corresponding primary, secondary, and tertiary amides in excellent yields. TBPB proved to be an efficient and highly chemoselective benzoylating reagent for aliphatic amines in the presence of aromatic amines/ hydroxyl groups.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380811.
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- 18 General Experimental Procedure for the Synthesis of Amide from Ammonia/Amine and TBPBA mixture of TBPB (1 mmol) and requisite aq NH3 or amine (1.1 mmol) were charged in a round-bottom flask. The reaction mixture was stirred at r.t. for the indicated time, and progress of the reaction was monitored by TLC/GC. The crude product was directly purified by column chromatography (silica gel, 100–200 mesh, PE–EtOAc) to provide the desired pure product. The identity of the compound was confirmed by 1H NMR and 13C NMR spectroscopic methods. N-(4-Methoxybenzyl)benzamide (3c) 17a 1H NMR (400 MHz, CDCl3): δ = 7.77 (d, J = 7.1 Hz, 2 H), 7.48 (t, J = 7.2 Hz, 1 H), 7.41 (t, J = 7.7 Hz, 2 H), 7.27 (d, J = 8.5 Hz, 2 H), 6.87 (d, J = 8.6 Hz, 2 H), 6.45 (br s, 1 H), 4.56 (d, J = 5.56 Hz, 2 H), 3.79 (s, 3 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 167.29, 159.11, 134.43, 131.50, 130.25, 129.31, 128.57, 126.95, 114.15, 55.31, 43.63 ppm. N-(4-Fluorobenzyl)benzamide (3e) 17a 1H NMR (400 MHz, CDCl3): δ = 7.78 (d, J = 8.0 Hz, 2 H), 7.49 (t, J = 7.3 Hz, 1 H), 7.40 (t, J = 7.7 Hz, 2 H), 7.31–7.25 (m, 2 H), 7.0 (t, J = 8.6 Hz, 2 H), 6.67 (br s, 1 H), 4.58 (d, J = 5.58 Hz, 2 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 167.45, 162.2 (d, J C–F = 244 Hz), 134.21, 134.07, 131.64, 129.53 (d, J C–F = 8 Hz), 128.60, 126.98, 115.56 (d, J C–F = 21 Hz), 43.33 ppm. N-(3-Chlorobenzyl)benzamide (3f) 17b 1H NMR (400 MHz, CDCl3): δ = 7.78 (d, J = 7.16 Hz, 2 H), 7.49 (t, J = 8.4 Hz, 1 H), 7.41 (t, J = 7.7 Hz, 2 H), 7.30 (s, 1 H), 7.25–7.18 (m, 3 H), 6.77 (br s, 1 H), 4.58 (d, J = 5.72 Hz, 2 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 167.54, 140.34, 134.52, 134.04, 131.71, 129.99, 128.62, 127.80, 127.68, 127.01, 125.89, 43.42 ppm. N-(4-Cyanobenzyl)benzamide (3g) 17c 1H NMR (400 MHz, CDCl3): δ = 7.80 (d, J = 7.9 Hz, 2 H), 7.59 (d, J = 6.6 Hz, 2 H), 7.52 (t, J = 7.3 Hz, 1 H), 7.45–7.41 (m, 4 H), 6.89 (br s, 1 H), 4.67 (d, J = 6.0 Hz, 2 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 167.67, 143.96, 133.76, 132.47, 131.93, 128.70, 128.19, 127.02, 118.73, 111.21, 43.48 ppm.