Hydrodehalogenation of halogenated pyridines and quinolines by sodium borohydride/N,N,N′,N′-tetramethylethylenediamine under palladium catalysis

被引：29

作者：

Chelucci, Giorgio ^{[1
]}

机构：

[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 12期

关键词：

Hydrodehalogenation; Reduction; Halopyridines; Haloquinolines; Palladium catalysts; Sodium borohydride; ROOM-TEMPERATURE; DEHALOGENATION;

D O I：

10.1016/j.tetlet.2010.01.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A protocol for the hydrodehalogenation of halogenated pyridines and quinolines by the sodium borohydride/N,N,N',N'-tetramethylethylenediamine (NaBH4-TMEDA) system under palladium catalysts is reported. Catalytic amounts of [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium(II) in combination with NaBH4-TMEDA rapidly hydrodehalogenate chloro(bromo)-pyridines and -quinolines at room temperature in quantitative yields. Chemoselective reduction of 4,7-dichloroquinoline affords 7-chloroquinoline as the sole product in almost quantitative yield. Moreover, palladium(II) acetate-triphenylphosphine and NaBH,TMEDA are able to reduce efficiently reactive bromo-pyridines and -quinolines. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1562 / 1565

页数：4

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