4.7 Article

Manganese(III)-Promoted Double Carbonylation of Anilines Toward α-Ketoamides Synthesis

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 3, Pages 487-492

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202101233

Keywords

Carbonylation; Double Carbonylation; alpha-Ketoamides; Manganese; Radical

Funding

  1. DICP

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A Mn(III)-promoted double carbonylation reaction using anilines and alkylborates or Hantzsch esters has been developed for the synthesis of alkyl alpha-ketoamides with excellent selectivity. The method provides a broad range of derivatives in moderate to good yields.
Employing anilines as nucleophiles in double carbonylation is a longstanding challenge. In this communication, a Mn(III)-promoted double carbonylation of alkylborates or Hantzsch esters with anilines toward the synthesis of alpha-ketoamides has been developed. By using easily available potassium alkyltrifluoroborates or Hantzsch esters as the starting material, and cheap and non-toxic Mn(OAc)(3)center dot 2H(2)O as the promotor, a broad range of alkyl alpha-ketoamide derivatives were synthesized in moderate to good yields with excellent selectivity.

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