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Nickel-Catalyzed Deaminative Acylation of Activated Aliphatic Amines with Aromatic Amides via C-N Bond Activation

Chu-Guo Yu1, Yutaka Matsuo1,2

  • 1Hefei National Laboratory for Physical Sciences at Microscale, and Department of Chemistry, School of Chemistry and Materials Science , University of Science and Technology of China , 96 Jinzhai Road , Hefei , Anhui 230026 , China.

Organic Letters
|January 22, 2020
PubMed

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Amines to Amides: Acylation of Amines01:19

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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