Stereospecific Suzuki, Sonogashira, and Negishi Coupling Reactions of N-Alkoxyimidoyl Iodides and Bromides
Debra D. Dolliver*, Bijay T. Bhattarai, Arjun Pandey, Megan L. Lanier, Amber S. Bordelon, Sarju Adhikari, Jordan A. Dinser, Patrick F. Flowers, Veronica S. Wills, Caroline L. Schneider, Kevin H. Shaughnessy, Jane N. Moore, Steven M. Raders, Timothy S. Snowden, Artie S. McKim, Frank R. Fronczek
*Department of Chemistry, The University of Alabama, Box
870336, Tuscaloosa, Alabama 35487-0336, United States, Email: ddolliver
selu.edu
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.
DOI: 10.1021/jo400179u
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Abstract
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.
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Key Words
Oximes, Suzuki coupling, Sonogashira coupling
ID: J42-Y2013-0980
