Stereospecific Suzuki, Sonogashira, and Negishi Coupling Reactions of N-Alkoxyimidoyl Iodides and Bromides
2013
Dolliver, Debra D. | Bhattarai, Bijay T. | Pandey, Arjun | Lanier, Megan L. | Bordelon, Amber S. | Adhikari, Sarju | Dinser, Jordan A. | Flowers, Patrick F. | Wills, Veronica S. | Schneider, Caroline L. | Shaughnessy, Kevin H. | Moore, Jane N. | Raders, Steven M. | Snowden, Timothy S. | McKim, Artie S. | Fronczek, Frank R.
A high-yielding stereospecific route to the synthesis of single geometric isomers of diaryl oxime ethers through Suzuki coupling of N-alkoxyimidoyl iodides is described. This reaction 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 to afford single geometric isomers of aryl alkynyl oxime ethers has also been developed. Several of these reactions proceed through copper-free conditions. The Negishi coupling of N-alkoxyimidoyl halides is introduced. The E and Z configurations of nine Suzuki-coupling products and two Sonogashira-coupling products were confirmed by X-ray crystallography.
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