Synthesis of Multisubstituted Benzenes from Phenols via Multi-substituted Benzynes

A new method to synthesize multifunctionalized arenes from simple phenols through aryne intermediates is described. Multisubstituted aryne precursors were prepared from phenols by Ir-catalyzed C-H borylation, deborylthiolation, O-triflylation, S-oxidation, and further modification through ortho-deprotonation directed by the sulfoxide moiety. Various multisubstituted arenes were synthesized by transformations of highly functionalized aryne intermediates generated from the o-sulfinylaryl triflates.

Automated summary

A new method for synthesizing multifunctionalized arenes from simple phenols using aryne intermediates is described. The aryne precursors were prepared from phenols through various transformations, and the highly functionalized aryne intermediates were used to synthesize multisubstituted arenes.