Sulfide‐Catalyzed Trifluoromethylthiolation‐Cyclization of Tryptamine Derivatives

Rui Guo*, Baohua Cai, Ming Yu Jin, Huaixue Mu, Jun Joelle Wang*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

9 Citations (Scopus)

Abstract

Trippy triptamines: An SCF3 group can be incorporated in tryptamine derivatives via a sulfide-catalyzed cascade trifluoromethylthiolation-cyclization. A series of C(3)-CF3S pyrrolidinoindolines were obtained in moderate to good yields under mild conditions. Furthermore, some enantioselectivity was observed when using chiral sulfide thiocineole as a catalyst.

A catalytic method for the incorporation of an SCF3 group to tryptamine derivatives was developed via a sulfide-catalyzed cascade trifluoromethylthiolation-cyclization. A series of C(3)-CF3S pyrrolidinoindolines were obtained in moderate to good yields under mild conditions. Furthermore, some enantioselectivity was observed when using chiral sulfide thiocineole as a catalyst.
Original languageEnglish
Pages (from-to)687-690
Number of pages4
JournalAsian Journal of Organic Chemistry
Volume8
Issue number5
Early online date25 Feb 2019
DOIs
Publication statusPublished - May 2019

User-Defined Keywords

  • organofluorine
  • trifluoromethylthiolation
  • cyclization
  • organocatalysis
  • pyrrolidinoindolines

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