Palladium-Catalyzed Cascade C-H Functionalization/Asymmetric Allylation Reaction of Aryl α-Diazoamides and Allenes: Lewis Acid Makes a Difference

Chemistry. 2022 Feb 19;28(11):e202104218. doi: 10.1002/chem.202104218. Epub 2022 Jan 28.

Abstract

A Pd-catalyzed cascade C-H functionalization/asymmetric allylation reaction with aryl α-diazoamides and allenes has been developed. The reaction provides an efficient approach to construct chiral 3,3-disubstituted oxindole derivatives in high levels of yield and enantioselectivity (up to 93 % ee). Notably, the chromium complex works as Lewis acid to facilitate the formation of palladium carbene and to enhance acidity of carboxylic acid, allowing for higher stereochemical control and efficiency.

Keywords: C−H functionalization; asymmetric allylation; chiral 3,3-disubstituted oxindoles; diazo compound.

MeSH terms

  • Alkadienes*
  • Catalysis
  • Lewis Acids
  • Palladium*

Substances

  • Alkadienes
  • Lewis Acids
  • propadiene
  • Palladium