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Enhancing Reactivity and Site-Selectivity in Hydrogen Atom Transfer from Amino Acid C-H Bonds via Deprotonation.
Organic Letters 2018 Februrary 3
A kinetic study on the reactions of the cumyloxyl radical (CumO• ) with N-Boc-protected amino acids in the presence of the strong organic base DBU has been carried out. CO2 H deprotonation increases the electron density at the α-C-H bonds activating these bonds toward HAT to the electrophilic CumO• strongly influencing the intramolecular selectivity. The implications of these results are discussed in the framework of HAT-based aliphatic C-H bond functionalization of amino acids and peptides.
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