Combining Photodeprotection and Ligation into a Dual-Color Gated Reaction System

Chemistry. 2020 Dec 18;26(71):16985-16989. doi: 10.1002/chem.202003546. Epub 2020 Oct 16.

Abstract

We report a photochemical reaction system which requires activation by two colors of light. Specifically, a dual wavelength gated system is established by fusing the visible light mediated deprotection of a dithioacetal with the UV light activated Diels-Alder reaction of an o-methylbenzaldehyde with N-ethylmaleimide. Critically, both light sources are required to achieve the Diels-Alder adduct, irradiation with visible or UV light alone does not lead to the target product. The introduced dual gated photochemical system is particularly interesting for application in light driven 3D printing, where two color wavelength activated photoresists may become reality.

Keywords: Diels-Alder; cycloaddition; photocatalysis; photooxidation; protecting groups.