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. Author manuscript; available in PMC: 2014 Apr 2.
Published in final edited form as: Angew Chem Int Ed Engl. 2013 Mar 4;52(14):3949–3952. doi: 10.1002/anie.201300763

Figure 2.

Figure 2

A. Direct difluoroethylation of heteroaromatic Michael acceptors and thiols. B. Direct difluoroethylation of an advanced intermediate from the Bristol-Myers Squibb compound library. C. A general synthesis of fluorinated heteroarylether bioisosteric reagents and a proof of concept on 2-quinoxalinol. Reagents and conditions: (a) reactions performed on 0.2 mmol scale, 40 (2.0 equiv), TBHP (5.0 equiv), TsOH•H2O (1.0 equiv), ZnCl2 (1.0 equiv), 0 to 23 °C, reaction completed in 24 h; (b) reactions performed on 0.1 mmol scale, 41 (1.5 equiv), TBHP (5.0 equiv), TsOH•H2O (1.0 equiv), ZnCl2 (1.5 equiv), reaction completed in 4 h at 0 °C after second addition of 41 (1.5 equiv), TBHP (5.0 equiv).