Abstract
The α-amidoalkylating properties of 1-(N-acylamino)alkyltriarylphosphonium salts with weakened Cα-P+ bond strength are discussed and examined. It is demonstrated that such type of phosphonium salts reacts smoothly with a diverse array of carbon- and heteroatom-based nucleophiles, including 1-morpholinocyclohexene, 1,3-dicarbonyl compounds, benzotriazole sodium salt, p-toluenesulfinate sodium salt, benzylamine, triarylphosphines, and other P-nucleophiles. Reactions are conducted at room temperature, in a short time (5–15 min) and mostly without catalysts. Simple work-up procedures result in good or very good yields of products. The structures of known compounds were established by spectroscopic methods and all new compounds have been fully characterized using 1H-, 13C-, 31P-NMR, IR spectroscopy, and high-resolution mass spectrometry. Mechanistic aspects of described transformations are also performed and discussed. It was demonstrated that unique properties make 1-(N-acylamino)alkyl-triarylphosphonium salts with weakened Cα-P+ bond strength interesting building blocks with great potential, especially in α-amidoalkylation reactions.
Highlights
Specific structural features of 1-(N-acylamino)alkylphosphonium salts make them very interesting reagents
We focus our studies on the reactivity of phosphonium salts 4 with weakened
Cα-P bond strength in α-amidoalkylation of various types of carbon- and heteronucleophiles, as shown in Scheme 2. 1-Morpholinocyclohexene and 1,3-dicarbonyl compounds, such as dimethyl shown in Scheme 2. 1-Morpholinocyclohexene and 1,3-dicarbonyl compounds, such as dimethyl malonate, diethyl malonate, and ethyl acetoacetate, are used as carbon nucleophiles
Summary
Specific structural features of 1-(N-acylamino)alkylphosphonium salts make them very interesting reagents. The presence of a positively charged nucleofugal phosphonium moiety in the close surroundings of the N-acyl group determines its unique chemical properties such as high reactivity in α-amidoalkylations [1,2,3,4,5,6,7,8,9,10] This type of reactions has enjoyed unflagging interest for years as a synthetic method with great potential, especially valuable for C-C and C-heteroatom bond formation [1,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37].
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