Easy Preparation of Alkyl Amides

Simple method for making amides from alkyl iodides, amines, and a CO source.


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A novel, mild and facile preparation of alkyl amides from unactivated alkyl iodides employing a fac-Ir(ppy)3-catalyzed radical aminocarbonylation protocol has been developed. Using a two-chambered system, alkyl iodides, fac-Ir(ppy)3, amines, reductants, and CO gas (released ex situ from Mo(CO)6), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a wide range of alkyl amides in moderate to excellent yields.

• Mild and Low-Pressure fac-Ir(ppy)₃-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis,
  Shiao Y. Chow, Marc Y. Stevens, Linda Åkerbladh, Sara Bergman, Luke R. Odell,
  Chem. Eur. J. 2016.
  DOI: 10.1002/chem.201601694

N-isopropylcyclohexanecarboxamide[2] (1a) (CAS 6335-52-0)
Prepared following the general procedure. Spectral data were in agreement with literature values. White solid (39 mg, 78%), Rf = 0.10 (10% EtOAc in n-pentane).

1H NMR (400 MHz, CDCl3): δ 5.19 (s, 1H), 4.07 (dt, J = 8.0, 6.6 Hz, 1H), 2.00 (tt, J = 11.7, 3.5 Hz, 1H), 1.89–1.72 (m, 4H), 1.74–1.52 (m, 1H), 1.48–1.35 (m, 2H), 1.31–1.18 (m, 3H), 1.13 (d, J = 6.6 Hz, 6H).

13C{1H} NMR (100 MHz, CDCl3): δ 175.4, 45.8, 41.1, 29.9, 25.9, 23.0. EI-MS: m/z 169.2.

2] O. Itsenko, T. Kihlberg, B. Långström, J. Org. Chem. 2004, 69, 4356–4360.

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