LUF5771

The cyclometalated Ir(III) complexes-catalyzed aerobic hydroxylation of arylboronic acids RB(OH)₂ (R = 4-cyanophenyl, naphthalen-1-yl, 9-phenyl-9H-carbazol-3-yl, etc.) under visible-light has been successfully developed.This catalytic system has a broad substrate scope, affording a series of phenols ROH smoothly with the highest isolated yield up to 95%.Moreover, this protocol is capable to synthesize several useful phenols containing bulky moieties, which are potential candidates or intermediates used as pharmaceuticals and functional materials.The Ir(III)-catalyzed hydroxylation of arylboronic acids could be applied in a one-pot synthesis of several important phenol derivatives, including 1,1'-methylene-bis(2-naphthol), 2,3-dihydro-1H-naphtho[2,1-e][1,3]oxazine and a bioactive compound 3,5-diphenylphenyl N-cyclopentylcarbamate.

A metal‐free approach to meta‐substituted phenols from cyclohex‐2‐enone via catalytic oxidative aromatization has been developed. The transformations are initiated with a catalytic amount of molecular iodine as the direct oxidant, while dimethyl sulfoxide is employed as the terminal oxidant. This practical approach is capable of avoiding the use of metal promoters and costly reagents, the lengthy synthesis, and overoxidation of products, and thus facilitates the efficient construction of meta‐substituted phenol derivatives from inexpensive commercial chemicals under mild conditions. The synthetic utility of this approach is evident in the de novo syntheses of two bioactive molecules with good total yields, in which easily available chemicals were employed, protective groups were not utilized, and no unwanted carbon atoms were removed in each step.magnified image