Microwave-Assisted Rhodium (III)-Catalyzed [3+3] Annulation of 2-Benzyl-2H-Indazole-6-carboxylic Acids with Iodonium Ylides: A Regioselective Synthesis of Indazole-Fused Chromenes

Hong Ren Chen, Indrajeet J. Barve, Hung Sheng Hsieh, Kuan Miao Liu, Ganesh P. Pawar, Chung Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A Rh(III)-catalyzed redox-neutral C−H activation/[3+3] cyclization of 2-benzyl-2H-indazole-6-carboxylic acids with iodonium ylides under microwave irradiation for the synthesis of indazole-fused chromenes has been reported. The critical feature of this method is that the C−H activation of the C7−H bond of 2-benzyl-2H-indazole-6-carboxylic acid proceeds regioselectively in the presence of the proximate C5−H bond without the need of external oxidant. Microwave irradiation reduced the reaction time as compared to conventional heating. The detailed mechanistic study disclosed the mechanistic pathway of the reaction.

Original languageEnglish
Article numbere202400756
JournalAdvanced Synthesis and Catalysis
Volume367
Issue number1
DOIs
StatePublished - 7 Jan 2025

Keywords

  • C−H activation
  • Indazole-fused chromenes
  • Iodonium ylides
  • Regioselective synthesis
  • [3+3] cyclization

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