Suzuki鈥揗iyaura Coupling Reactions of Iodo(difluoroenol) Derivatives, Fluorinated Building Blocks Accessible at Near-Ambient Temperatures

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• 作者：Peter G. Wilson ; Jonathan M. Percy ; Joanna M. Redmond ; Adam W. McCarter
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：August 3, 2012
• 年：2012
• 卷：77
• 期：15
• 页码：6384-6393
• 全文大小：444K
• 年卷期：v.77,no.15(August 3, 2012)
• ISSN：1520-6904

文摘

A recently developed method for the near-ambient generation of difluorovinylzinc reagents has facilitated the preparation of 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro-1-iodoethene and 2,2-difluoro-1-iodo-1-(2鈥?methoxyethoxymethoxy)ethene. The utility of these reagents has been investigated in Suzuki鈥揗iyaura couplings with a range of potassium trifluoroborate coupling partners, with the scope of successful couplings proving wide. Deiodinated species appeared as significant side products, but a solvent change from i-PrOH to t-BuOH suppressed the pathway to these species and improved coupling yields.