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Visible Light-Mediated Oxidative Debenzylation
preprintsubmitted on 23.10.2020, 15:06 and posted on 27.10.2020, 06:20 by Cristian Cavedon, Eric T. Sletten, Amiera Madani, Olaf Niemeyer, Peter H. Seeberger, Bartholomäus Pieber
Protecting groups are key in the synthesis of complex molecules such as carbohydrates to distinguish functional groups of similar reactivity. The harsh conditions required to cleave stable benzyl ether protective groups are not compatible with many other protective and functional groups. The mild, visible light-mediated debenzylation disclosed here renders benzyl ethers orthogonal protective groups. Key to success is the use of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as stoichiometric or catalytic photooxidant such that benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time for this transformation can be reduced from hours to minutes in continuous flow.