Abstract
Summary Substantial effort is currently being devoted to selective C(sp3)–H bond functionalization, and photocatalysis has presented enormous potential opportunities in this research field. Here, we developed a visible-light-induced functionalization of unactivated C(sp3)–H bonds via the synergistic effects of an organo-photoredox catalyst and a bromine-based hydrogen atom transfer agent. By applying CH2Br2 as both the solvent and the bromine radical source, the alkylation and amination of tertiary C(sp3)–H bonds were achieved in a highly selective fashion. This study represents the first example of selective activation of unactivated alkanes by bromine radicals in a catalytic and metal-free manner. Good reactivity was achieved by using a sealed microtubing reactor or by adding a proper amount of water. This highly selective C(sp3)–H functionalization protocol offers a new paradigm for the direct synthesis of valuable compounds from abundant alkane feedstocks in a convenient and green manner.
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