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

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• 作者：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
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：April 19, 2013
• 年：2013
• 卷：78
• 期：8
• 页码：3676-3687
• 全文大小：476K
• 年卷期：v.78,no.8(April 19, 2013)
• ISSN：1520-6904

文摘

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.