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Mechanism of Nickel-Catalyzed Suzuki-Miyaura Coupling of Amides

Zheng-Yang Xu1, Hai-Zhu Yu2, Yao Fu1

  • 1Collaborative Innovation Centre of Chemistry for Energy Materials, CAS Key Laboratory of Urban Pollutant Conversion, Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.

Chemistry, an Asian Journal
|May 9, 2017
PubMed

Keywords:
C-N activationSuzuki-Miyaura couplingdensity functional calculationsnickelreaction mechanisms

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Preparation of Amides01:29

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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
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Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
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Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
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