Unlocking the Reactivity of Diazo Compounds on Red Light with the Use of Photochemical Tools

31 August 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Photoinduced bioorthogonal reactions constitute a valuable class of chemical transformations that enable spatiotemporal con-trol of biomacromolecules. Among them, those involving carbenes proved effective in various bioapplications, but they require ultraviolet or blue-light irradiation. Using lower energetic radiation, however, offers deeper penetration and diminishes photo-damages. Thus, herein, we describe the photochemistry of structurally diversified diazo reagents under red light irradiation. Reactive intermediates can be generated via direct photolysis or taking advantage of porphyrin chemistry via photosensitisa-tion and photoredox catalysis.

Keywords

photocatalysis
diazo compounds
carbene chemistry
radicals

Supplementary materials

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Supporting information
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Full description of optimization and mechanistic studies, gen-eral procedures, compound characterization (NMR, HRMS), and NMR spectra (PDF).
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