Aluminum-Catalyzed Cross-Coupling of Silylalkynes with Aliphatic C-F Bonds

被引：36

作者：

Jaiswal, Amit K. ^{[1
]}

Goh, Kelvin K. K. ^{[1
]}

Sung, Simon ^{[1
]}

Young, Rowan D. ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 07期

关键词：

ARYL GRIGNARD-REAGENTS; ALKYL FLUORIDES; OLEFIN POLYMERIZATION; ACTIVATION; ORGANOZINC; CHEMISTRY; PALLADIUM; HALIDES; LIGAND; CATION;

D O I：

10.1021/acs.orglett.7b00712

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the generation of aliphatic and benzylic acetylenes via reaction of primary, secondary, and tertiary aliphatic fluorides with various trimethylsilyl acetylides. These reactions are catalyzed by Al arid B Lewis acids, most,effectively by the extremely fluorophilic tris(pentafluorophenyl)alane, representing the first example of catalytic incorporation of alkynes into aliphatic C-F positions. The fluorophilicity of the catalysts gives rise to fluorine selectivity over other halogens, allowing orthogonal reactivity pathways.

引用

页码：1934 / 1937

页数：4

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