Selective synthesis of 2-aryl-3-alkenylindoles and 2-aryl-3-alkynylindoles by palladium-catalyzed ligand-promoted annulative coupling of anilines and propargyl alcohols

A palladium-catalyzed annulative reaction between aniline and propargyl alcohol has been developed. Propargyl alcohols act as internal or terminal alkynes in the reactions through C & minus;H/C & minus;C activation in the presence of Ac-Gly-OH or Xantphos as ligand, resulting in the formation of 3-alkenylindoles or 3-alkynylindoles respectively. The incorporated alkenyl and alkynyl groups could be engaged for further derivations to form versatile indole skeletons with potential applications. (c) 2021 Elsevier B.V. All rights reserved.

Automated summary

A palladium-catalyzed annulative reaction between aniline and propargyl alcohol has been developed, resulting in versatile indole skeletons with potential applications. The reaction utilizes propargyl alcohols as internal or terminal alkynes for the formation of 3-alkenylindoles or 3-alkynylindoles through C-H/C-C activation.