- Amide formation using in situ activation of carboxylic acids with [Et 2NSF2]BF4
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The formation of amides through the in situ activation of carboxylic acids with [Et2NSF2]BF4 is presented. A wide range of carboxylic acids and amines were used to produce the corresponding amides in up to 99 % yield. The reaction of hindered amines was also possible in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under slightly modified conditions. An enantiopure carboxylic acid and amine were both shown to react without racemization. Copyright
- Mahe, Olivier,Desroches, Justine,Paquin, Jean-Francois
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p. 4325 - 4331
(2013/07/26)
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- A Study of the Ferrous Ion-initiated SRN1 Reactions of Halogenoarenes with tert-Butyl Acetate and N-Acylmorpholine Enolates
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A detailed preparative study is reported of the ferrous ion-initiated SRN1 reactions of a range of halogenoarenes with the sodium enolates of tert-butyl acetate, n-acetylmorpholine and a number of higher N-acylmorpholines.Smooth and rapid substitution occurs in many cases, and good to excellent yields were obtained of arylacetic esters or acids, arylacetamides and arylalkanamides.The broad scope and limitations of the process have been defined, and the possible role of the ferrous ion is discussed.
- Leeuwen, Milko van,McKillop, Alexander
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p. 2433 - 2440
(2007/10/02)
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- Photostimulated Reactions of N,N-Disubstituted Amide Enolate Anions with Haloarenes by the SRN1 Mechanism in Liquid Ammonia
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The photostimulated reactions of chloro-, bromo-, and iodobenzenes, 1-chloronaphthalene, and 9-bromophenanthrene with the enolate anion of N-methyl-N-phenylacetamide in liquid ammonia gave good yields of substituted products.In the dark, iodobenzene gave 34percent of substitution product, but chlorobenzene did not react.The enolate anion of N,N-dimethylacetamide was only partially soluble in liquid ammonia, but good yields of substitution products were obtained.The enolate anion of N-acetylpiperidine was insoluble in liquid ammonia, but the enolate anion of N-acetylmorpholine was soluble and good yields of substitution products were obtained under photostimulation.It is suggested that these reactions occur by the SRN1 mechanism of aromatic substitution.
- Rossi, Roberto A.,Alonso, Ruben A.
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p. 1239 - 1241
(2007/10/02)
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