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Synthesis of Oximes

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The Suzuki coupling of N-alkoxyimidoyl iodides occurs with complete retention of the imidoyl halide geometry to give single E- or Z-isomers of diaryl oxime ethers. The Sonogashira coupling of N-alkoxyimidoyl iodides and bromides with a wide variety of terminal alkynes affords single geometric isomers of aryl alkynyl oxime ethers.
D. D. Dolliver, B. T. Bhattarai, A. Pandey, M. L. Lanier, A. S. Bordelon, S. Adhikari, J. A. Dinser, P. F. Flowers, V. S. Wills, C. L. Schneider, K. H. Shaughnessy, J. N. Moore, S. M. Raders, T. S. Snowden, A. S. McKim, F. R. Fronczek, J. Org. Chem., 2013, 78, 3676-3687.


D. D. Dolliver, B. T. Bhattarai, A. Pandey, M. L. Lanier, A. S. Bordelon, S. Adhikari, J. A. Dinser, P. F. Flowers, V. S. Wills, C. L. Schneider, K. H. Shaughnessy, J. N. Moore, S. M. Raders, T. S. Snowden, A. S. McKim, F. R. Fronczek, J. Org. Chem., 2013, 78, 3676-3687.


Hydroboration with catecholborane, followed by treatment with easily available reagents such as alkenyl sulfones or alkynyl phenyl sulfones in the presence of a radical initiator, represents an effective and simple one-pot procedure for direct vinylation, formylation, and cyanation.
A.-P. Schaffner, V. Darmency, P. Renaud, Angew. Chem. Int. Ed., 2006, 45, 5847-5849.