Site-Tunable Csp3-H Bonds Functionalization by Visible-Light-Induced Radical Translocation of N-Alkoxyphthalimides.

Abstract

Site-tunable functionalization of C(sp3)-H bonds has been accomplished through radical translocation and cross-coupling. Upon irradiation with visible light, copper-based photocatalyst [Cu(Xantphos)(dmp)]BF4 enabled cross-coupling of N-alkoxyphthalimides with amino acid esters or amino acids to provide δ-C(sp3)-H alkylated alcohols (31 examples, up to 92% yield) with additive BNDHP or α-C(sp3)-H alkylated alcohols (18 examples, up to 86% yield) with additive DABCO in a highly regioselective fashion.