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Suzuki−Miyaura coupling reactions of iodo(difluoroenol) derivatives, fluorinated building blocks accessible at near-ambient temperatures

Wilson, Peter G and Percy, Jonathan M and Redmond, Joanna and McCarter, Adam W. (2012) Suzuki−Miyaura coupling reactions of iodo(difluoroenol) derivatives, fluorinated building blocks accessible at near-ambient temperatures. Journal of Organic Chemistry, 77 (15). pp. 6384-6393. ISSN 0022-3263

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Abstract

A recently developed method for the nearambient generation of difluorovinylzinc reagents has facilitated the preparation of 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro-1 - i o d o e t h e n e and 2 , 2 - d i fl u o r o - 1 - i o d o - 1 - ( 2 ′ - methoxyethoxymethoxy)ethene. The utility of these reagents has been investigated in Suzuki−Miyaura 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.