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.

中文翻译：

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可见光介导的氧化脱苄基作用

保护基是合成复杂分子（例如碳水化合物）以区分具有相似反应性的官能团的关键。裂解稳定的苄基醚保护基所需的苛刻条件与许多其他保护和官能基不相容。本文公开的温和的，可见光介导的脱苄基作用使苄基醚具有正交保护基团。成功的关键是使用2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）作为化学计量的或催化的光氧化剂，这样在叠氮化物，烯烃和炔烃的存在下可以裂解苄基醚。在连续流动中，这种转化的反应时间可以从数小时减少到数分钟。