Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany.
Department of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany.
Org Lett. 2021 Jan 15;23(2):514-518. doi: 10.1021/acs.orglett.0c04026. Epub 2021 Jan 5.
The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow.
苄醚的催化氢解或伯奇还原的裂解存在官能团兼容性差的问题，限制了它们作为保护基的应用。这里揭示的可见光介导的去苄基作用使苄醚成为暂时的保护基，从而实现了新的正交保护策略。使用 2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）作为化学计量或催化光氧化剂，在叠氮化物、烯烃和炔烃存在下可以裂解苄醚。在连续流中，反应时间可以从数小时缩短到数分钟。
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