Stereospecific Suzuki, Sonogashira, and Negishi Coupling Reactions of N-Alkoxyimidoyl Iodides and Bromides

…, AS Bordelon, S Adhikari, JA Dinser…

Index: 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. Journal of Organic Chemistry, 2013 , vol. 78, # 8 p. 3676 - 3687

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Citation Number: 11

Abstract

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 ...

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