Direct Access to Sulfonamidated-1,4-Benzoquinones via Sulfonamidation of Aryl Alcohol-Derived Quinone Monoacetals.

An alcohol-derived quinone monoacetal (QMA)-enabled strategy for the direct synthesis of sulfonamidated benzoquinones via a nucleophilic addition-elimination sequence using N-methoxy sulfonamides as reagents is reported. QMA serves as a uniquely competent surrogate of benzoquinone. The protocol exhibits broad substrate scope, excellent functional group tolerance, and gram-scale applicability. Mechanistic studies, supported by DFT calculations, reveal that acid-promoted acetal hydrolysis followed by tautomerization-assisted methanol elimination is the key step governing product formation.