Synthesis of meta‐Arylated Phenol Derivatives by Rhodium(I)‐Catalyzed Arylation of Quinone Monoacetal

Abstract

The first selective synthesis of metaarylphenol derivatives by arylation of quinone monoacetal is reported. The transformation was achieved under Rh(I) catalysis via a formal arylation/demethoxylation process, and valuable metaarylphenols were obtained in high yields under mild conditions. Remarkably, an unprecedented convergent reaction pathway was assumed to be involved.

Molecular Complexity from Aromatics: Recent Advances in the Chemistry of paraQuinol and Masked para‐Quinone Monoketal

“…This method was also found very suitable for getting meta-diarylated phenol 125 (Scheme 14). [54] A three-component reaction of para-quinone monoketal 126, α-amino acid 127, and diaryl phosphine oxide was reported by a group of Shen, which introduced 3-(diarylphosphinyl)anilide 128 and N-aryl-2-diarylphosphinylpyrrolidine 129 to the aromatic system very selectively. It was proposed that this transformation may involve the in situ generations of 2-azaallyl anion or conjugated azomethine ylides through decarboxylation from the reaction between compound 126 and α-amino acid which were then trapped by diaryl phosphine oxide (Scheme 15).…”

Silver(I)-Catalyzed Enyne Cyclization/Aromatization of Alkyne-Tethered Cyclohexadienones to Access Meta-Substituted Phenols

“…In 2003, Smith and coworkers developed a one-pot C–H activation/borylation/oxidation strategy to access meta-substituted phenols with the influence of steric hindrance instead of the electronic effect . Later, Stahl et al elegantly reported the synthesis of meta-substituted phenols via the aerobic oxidative Heck/dehydrogenation of cyclohexenones (Scheme a) . Alternatively, the catalytic dehydrogenation of substituted cyclohexanones has also received considerable attention .…”