Light-Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single-Electron Oxidation with TEDA2+.

被引：32

作者：

Troyano, Francisco Jose Aguilar ^{[1
]}

Ballaschk, Frederic ^{[1
]}

Jaschinski, Marcel ^{[1
]}

Oezkaya, Yasemin ^{[1
]}

Gomez-Suarez, Adrian ^{[1
]}

机构：

[1] Berg Univ Wuppertal, Organ Chem, Gausstr 20, D-42119 Wuppertal, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 62期

关键词：

fluorination; mechanistic studies; organic synthesis; photochemistry; radicals; NUCLEOPHILIC AROMATIC-SUBSTITUTION; ENANTIOSELECTIVE TOTAL SYNTHESES; FLUORINATION REACTIONS; CARBOXYLIC-ACIDS; BOND FORMATION; CATALYSIS; FLUORIDES; OXALATES; IMINIUM; ENABLES;

D O I：

10.1002/chem.201903702

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of tertiary alkyl fluorides through a formal radical deoxyfluorination process is described herein. This light-mediated, catalyst-free methodology is fast and broadly applicable allowing for the preparation of C-F bonds from (hetero)benzylic, propargylic, and non-activated tertiary alcohol derivatives. Preliminary mechanistic studies support that the key step of the reaction is the single-electron oxidation of cesium oxalates-which are readily available from the corresponding tertiary alcohols-with in situ generated TEDA(2+.) (TEDA: N-(chloromethyl)triethylenediamine), a radical cation derived from Selectfluor (R).

引用

页码：14054 / 14058

页数：5

共 13 条

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