A General Strategy for C(sp3)–H Functionalization with Nucleophiles Using Methyl Radical as a Hydrogen Atom Abstractor [post]

Isabelle Leibler, Makeda A. Tekle-Smith, Abigail Doyle
2021 unpublished
We have developed a photocatalytic method that employs widely available, low-cost nucleophiles and a readily accessible HAT precursor for C(sp<sup>3</sup>)–H fluorination, chlorination, etherification, thioetherification, azidation, and carbon–carbon bond formation. Mechanistic studies are consistent with methyl radical-mediated HAT and linear free-energy relationships suggest that radical oxidation influences site-selectivity. Furthermore, this approach was highly effective for the
more » ... for the construction of multi-halogenated scaffolds and the late-stage functionalization of several bioactive molecules and pharmaceuticals with tunable regioselectivity.
doi:10.26434/chemrxiv.13644218 fatcat:mgnikrpudrbwdaynzimr7lg3n4