Photocatalyzed Benzylic Fluorination: Shedding "Light" on the Involvement of Electron Transfer

被引：99

作者：

Bloom, Steven ^{[1
]}

McCann, Michael ^{[1
]}

Lectka, Thomas ^{[1
]}

机构：

[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 24期

基金：

美国国家科学基金会;

关键词：

C-H BONDS; POSITIVE HALOGEN COMPOUNDS; MECHANISTIC ASPECTS; ARYLACETIC ACIDS; HYDROGEN; TOLUENE; STATE; DODECATUNGSTOCOBALTATE(III); 1,2,4,5-TETRACYANOBENZENE; COMPLEXES;

D O I：

10.1021/ol503094m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photocatalyzed oxidation of benzylic compounds by 1,2,4,5-tetracyanobenzene (TCB) in the presence of Selectfluor provides a synthetically efficient route to electron deficient, less substituted, and otherwise inaccessible benzylic fluorides. The virtue of this system is multifold: it is metal-free and mild, and the reagents are inexpensive. Mechanistically, the data suggest the intimate formation of intermediate radical cations in the key radical forming step, as opposed to a concerted hydrogen atom transfer process.

引用

页码：6338 / 6341

页数：4

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