Aerobic oxidative synthesis of benzimidazoles by flavin photocatalysis.

Flavin photocatalysis were utilised for an aerobic oxidative reaction between arylamines and o-phenylenediamine. This metal-free reaction proceeded in methanol under visible light irradiation and consumed only atmospheric molecular oxygen, providing a novel eco-friendly method for the synthesis of benzimidazoles.

Chiral Supramolecular Organogel Constructed Using Riboflavin and Melamine: Its Application in Photo-Catalyzed Colorimetric Chiral Sensing and Enantioselective Adsorption.

The synthesis of a chiral supramolecular organogel via the hierarchical helical self-assembly of optically active riboflavin and melamine derivatives is described herein. Owing to the photocatalysis of riboflavin and the supramolecular chirality induced in the helically stacked riboflavin/melamine complex, the gel is observed to act as a light-stimulated chiral sensor of optically active alcohols by detecting the change in color from yellow to green. The gel also served as an efficient chiral adsorbent, enabling optical resolution of a racemic compound with high chiral recognition ability.

Atom-Economical Syntheses of Dihydropyrroles Using Flavin-Iodine-Catalyzed Aerobic Multistep and Multicomponent Reactions.

Herein, we report facile, atom-economical syntheses of multisubstituted 2,3-dihydropyrroles using flavin-iodine-catalyzed aerobic oxidative multistep transformations of chalcones with ß-enamine ketones or 1,3-dicarbonyl compounds and amines. Exploiting coupled flavin-iodine catalysis, the multistep reaction, including C-C and C-N bond formation, is promoted only by the consumption of O2 (1 atm), thus allowing aerobic oxidative synthesis that generates green H2O as the only waste.

Aerobic cross-dehydrogenative coupling of toluenes and o-phenylenediamines by flavin photocatalysis for the facile synthesis of benzimidazoles.

Herein, we demonstrate a green atom-economical synthesis of benzimidazoles via the flavin-photocatalysed aerobic oxidative cross-dehydrogenative coupling of toluenes and o-phenylenediamines. The proposed metal-free reaction proceeds in methanol/H2O under visible light irradiation by consuming only molecular oxygen from atmospheric air and produces only water as waste.

Aerobic Oxidative C-H Azolation of Indoles and One-Pot Synthesis of Azolyl Thioindoles by Flavin-Iodine-Coupled Organocatalysis.

The aerobic oxidative cross-coupling of indoles with azoles driven by flavin-iodine-coupled organocatalysis has been developed for the green synthesis of 2-(azol-1-yl)indoles. The coupled organocatalytic system enabled the one-pot three-component synthesis of 2-azolyl-3-thioindoles from indoles, azoles, and thiols in an atom-economical manner by utilizing molecular oxygen as the only sacrificial reagent.

Phototropin-Inspired Chemoselective Synthesis of Unsymmetrical Disulfides: Aerobic Oxidative Heterocoupling of Thiols Using Flavin Photocatalysis.

Inspired by the photochemical mechanism of a plant blue-light receptor, a unique flavin-based photocatalytic system was developed for the chemoselective heterocoupling of two different thiols, which enabled the facile synthesis of unsymmetrical disulfides. Owing to the redox- and photo-organocatalysis of flavin, the coupling reaction took place under mild metal-free conditions and visible light irradiation with the use of air, which is recognized as the ideal green oxidant.