Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups,Organic Letters

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Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups
Organic Letters ( IF 4.9 ) Pub Date : 2021-01-05 , DOI: 10.1021/acs.orglett.0c04026
Cristian Cavedon _{1,

2} , Eric T Sletten ₁ , Amiera Madani _{1,

2} , Olaf Niemeyer ₁ , Peter H Seeberger _{1,

2} , Bartholomäus Pieber ₁

Affiliation

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.

中文翻译：

可见光介导的氧化脱苄基作用使得能够使用苄基醚作为临时保护基团

通过催化氢解或 Birch 还原裂解苄基醚存在官能团相容性差的问题，限制了它们作为保护基团的用途。本文公开的可见光介导的脱苄基作用使苄基醚成为临时保护基团，从而实现新的正交保护策略。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，可以在叠氮化物、烯烃和炔烃存在下裂解苄基醚。在连续流动中，反应时间可以从几小时缩短至几分钟。

更新日期：2021-01-16

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