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

被引：51

作者：

Cavedon, Cristian ^{[1
,2
]}

Sletten, Eric T. ^{[1
]}

Madani, Amiera ^{[1
,2
]}

Niemeyer, Olaf ^{[1
]}

Seeberger, Peter H. ^{[1
,2
]}

Pieber, Bartholomaeus ^{[1
]}

机构：

[1] Max Planck Inst Colloids & Interfaces, Dept Biomol Syst, D-14476 Potsdam, Germany

[2] Free Univ Berlin, Dept Chem & Biochem, D-14195 Berlin, Germany

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 02期

关键词：

DDQ; DEPROTECTION; AMINATION; VERSATILE; METAL;

D O I：

10.1021/acs.orglett.0c04026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：514 / 518

页数：5

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