Synthesis of acyl fluorides via photocatalytic fluorination of aldehydic C-H bonds

被引：66

作者：

Meanwell, Michael ^{[1
]}

Lehmann, Johannes ^{[1
]}

Eichenberger, Marc ^{[2
]}

Martin, Rainer E. ^{[2
]}

Britton, Robert ^{[1
]}

机构：

[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada

[2] F Hoffmann La Roche Ltd, Roche Innovat Ctr Basel, Roche Pharma Res & Early Dev pRED, Med Chem, Grenzacherstr 124, CH-4070 Basel, Switzerland

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 71期

关键词：

N-FLUOROBENZENESULFONIMIDE; CARBOXYLIC-ACIDS; MEDICINAL CHEMISTRY; DECATUNGSTATE ANION; EXCITED-STATE; REAGENT; OXIDATION; DERIVATIVES; ACTIVATION; REACTIVITY;

D O I：

10.1039/c8cc06375c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Acyl fluorides are versatile acylating agents owing to their unique stability. Their synthesis, however, can present challenges and is typically accomplished through deoxyfluorination of carboxylic acids. Here, we demonstrate that acyl fluorides can be prepared directly from aldehydes via a C(sp(2))-H fluorination reaction involving the inexpensive photocatalyst sodium decatungstate and electrophilic fluorinating agent N-fluorobenzenesulfonimide. This convenient fluorination strategy enables direct conversion of aliphatic and aromatic aldehydes into acylating agents.

引用

页码：9985 / 9988

页数：4

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