4-(Dimethylamino)pyridine as Multivalent Catalyst in Organic Synthesis

被引:2
|
作者
Freitas, Rosana Helena C. N. [1 ]
Rodrigues da Rocha, David [1 ]
机构
[1] Univ Fed Fluminense, Inst Quim, Campus Valonguinho, BR-24020141 Niteroi, RJ, Brazil
关键词
ONE-POT SYNTHESIS; DMAP SYNTHESIS; ESTERIFICATION; DERIVATIVES; CYCLIZATION;
D O I
10.1071/CH20204
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
4-(Dimethylamino)pyridine (DMAP) is an common and well-known catalyst in organic synthesis.([1,2]) It has basic and nucleophilic character, commonly exploited in reactions.([3,4]) DMAP has moderate aqueous solubility, which allows it to be used in aqueous reactions for green chemistry.([5,6]) Despite being toxic, DMAP is a versatile and inexpensive catalyst, able to promote different types of reactions with an emphasis on heterocycle synthesis,([7-15]) cycloadditions,([7,8]) multicomponent reactions (MCRs),([10,13,14,16,17]) and acylation reactions.([1,18-21]) It is also worth noting its growing use as a catalyst in stereoselective reactions.([7,22,23]) There are several methods for DMAP synthesis.([24,25]) An efficient protocol that provides DMAP (1) (Scheme 1) in high yield involves nucleophilic aromatic substitution (SNAr) of 4-chloropyridine hydrochloride (2) and dimethylamine in 1,4-dioxane and sodium hydroxide at 70 degrees C under pressure.([24]) Other methods such as continuous flow, which is a fast and economical protocol,([26]) can lead to successful DMAP synthesis. In this SNAr protocol,([25]) a nucleophile is formed through a reaction between DMF and NH3, which is then added to 4-chloropyridine hydrochloride (1) at high temperature and pressure to synthesize DMAP in 78% yield (Scheme 1).([25])
引用
收藏
页码:364 / 366
页数:3
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