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  1. ; ; ; ; (, Nature Communications)
    Abstract Radical substitution is a useful method to functionalize heterocycles, as in the venerable Minisci reaction. Empirically observed regiochemistries indicate that the CF2H radical has a nucleophilic character similar to alkyl radicals, but the CF3radical is electrophilic. While the difference between •CH3and •CF3is well understood, the reason that one and two Fs make little difference but the third has a large effect is puzzling. DFT calculations with M06-2X both reproduce experimental selectivities and also lead to an explanation of this difference. Theoretical methods reveal how the F inductive withdrawal and conjugative donation alter radical properties, but only CF3becomes decidedly electrophilic toward heterocycles. Here, we show a simple model to explain the radical orbital energy trends and resulting nucleophilicity or electrophilicity of fluorinated radicals. 
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  2. ; ; ; ; ; ; ; (, Angewandte Chemie International Edition)
    Abstract Synthetic organic electrochemistry is recognized as one of the most sustainable forms of redox chemistry that can enable a wide variety of useful transformations. In this study, readily prepared pyrolytic carbon electrodes are explored in several powerful rAP transformations as well as C−C and C−N bond forming reactions. Pyrolytic carbon provides an alternative to classic amorphous carbon‐based materials that are either expensive or ill‐suited to large‐scale flow reactions. 
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