Palladium-catalyzed chemoselective cross-coupling of acyl chlorides and organostannanes

被引：85
作者：
Lerebours, R [1 ]
Camacho-Soto, A [1 ]
Wolf, C [1 ]
机构：
[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 21期
关键词：
D O I：
10.1021/jo051257o
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHIC] Chemoselective cross-coupling of aliphatic and aromatic acyl chlorides with aryl-, heteroaryl-, and alkynylstannanes proceeds in up to 98% yield using 2.5 mol % of bis(di-tertbutylchlorophosphine)palladium(II) dichloride as the precatalyst. Various functional groups including aryl chlorides and bromides that usually undergo oxidative addition to palladium complexes bearing phosphinous acid or dialkylchlorophosphine ligands are tolerated. This procedure allows convenient ketone formation and eliminates inherent limitations of Friedel-Crafts acylations such as substituent-directing effects and typical reactivity requirements of Lewis acid-catalyzed electrophilic aromatic substitutions.
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收藏
页码：8601 / 8604
页数：4
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