Tuning the Photophysical Properties of Flavins by Attaching an Aryl Moiety via Direct C–C Bond Coupling

Abstract

Palladium-catalyzed Suzuki reactions of brominated flavin derivatives (5-deazaflavins, alloxazines, and isoalloxazines) with boronic acids or boronic acid esters that occur readily under mild conditions were shown to be an effective tool for the synthesis of a broad range of 7/8-arylflavins. In general, the introduction of an aryl/heteroaryl group by means of a direct C−C bond has been shown to be a promising approach to tuning the photophysical properties of flavin derivatives. The aryl substituents caused a bathochromic shift in the absorption spectra of up to 52 nm and prolonged the fluorescence lifetime by up to 1 order of magnitude. Moreover, arylation of flavin derivatives decreased their ability to generate singlet oxygen.

Silver-Promoted Rapid Synthesis of 3-Arylindan-1-ones: Microwave-Assisted Reductive Coupling of N-Tosylhydrazone and Boronic Acids

“…Formations of carbon–carbon bonds are a fundamental, however pivotal, process which is an essential drive for natural product synthesis and synthetic medicinal chemistry . This involves combining an electrophile and a nucleophile in the presence of a metal catalyst, constituting a typical cross-coupling reaction .…”