Palladium‐Catalyzed Direct CH Functionalization of Benzoquinone

Abstract

A direct Pd-catalyzed C=H functionalization of benzoquinone (BQ) can be controlled to give either mono- or disubstituted BQ, including the installation of two different groups in a one-pot procedure. BQ can now be directly functionalized with aryl, heteroaryl, cycloalkyl, and cycloalkene groups and, moreover, the reaction is conducted in environmentally benign water or acetone as solvents.

Supramolecular Ensemble of Aggregates of Pentacenequinone Derivative and Cadmium NPs: A Potential Catalytic/Photocatalytic System for Direct C‐H Activation of Quinones and Azoles

“…It is important to mention here that reaction was carried out without any oxidant. The previously reported approaches require presence of an oxidant for carrying out difunctionalization reactions of quinones . Under the above mentioned conditions, we carried out various reactions using a variety of boronic acids having electron donating and withdrwing substituents and in all these cases a preference for 2,6‐disubstituted product 9 was observed (PS36‐S49, Supporting Information).…”

“…Interestingly, after 24 h, 2,6‐disubstituted product was obtained in good yield. However, the conventional methods reported in literature for the hetero‐difunctionalization of quinones lack selectivity …”

Synthesis of Tetra(3‐thienyl)biphenoquinone and its Charge Transfer Complex with Perylene

“…[12] In contrastt ot he widely used oligothiophenes, few thiophene-substituted redox molecules have been reported so far, examples of which include tetrathiafulvalene [13] and p-benzoquinone (see below). [14] Aside from the electronic perturbations between biphenoquinone and thiophene,t he shape of thiophene,t hat is, af ive-membered ring, is fascinating. If the thermal intramolecular ring-closure reactiono ccurs in as imilar manner to 2,adoptingt hat reaction would simplify the synthesis of heteropentalene fragments, that is, the formation of thieno [3,2-b]benzofuran-,t hieno [2,3-b]benzofuran-, and thieno [3,4-b]benzofuran-containing molecules 12, 13,a nd 14, respectively (Scheme 2(b)).…”

Catalytic Electrophilic Alkylation of p‐Quinones through a Redox Chain Reaction

“…[9] Functionalized hydroquinone precursors can also be obtained through nucleophilic addition [10] and cycloaddition reaction [11] of simple quinones to substituted 2-cyclohexen-1,4-dione intermediates,w hich can then rearrange to hydroquinone and be oxidized. [16] However,benzylation of quinones remains challenging.H erein, we report am ild, one-step, redox-economical [17] catalytic allylation and benzylation of pquinones and the study of its unique mechanism, in which allyl and benzyl esters serve as the electrophiles and quinones are the formal "nucleophiles" (Scheme 1). [16] However,benzylation of quinones remains challenging.H erein, we report am ild, one-step, redox-economical [17] catalytic allylation and benzylation of pquinones and the study of its unique mechanism, in which allyl and benzyl esters serve as the electrophiles and quinones are the formal "nucleophiles" (Scheme 1).…”