Synthesis of 2-Arylphenols via Formal Bismuth(V)-Mediated C–O Arylation of Guaiacols

We report a new C-O arylation strategy for the synthesis of 2-arylphenols from bio-abundant guaiacols. Functionalization of the strong C-O bond is achieved through a sequence of arylative dearomatization, mediated selectively by an electrophilic bismuth(V) arylating agent, followed by 1,2-reduction and deoxygenative rearomatization. This methodology represents a rare example of complexity-generating deoxygenation applied to lignin-derived biorefinery feedstocks and provides independence from the regioselectivity rules established for the bismuth(V)-mediated arylation of simple phenols.