Indazolin-3-ylidenes (Indy*): easily accessible, sterically-hindered indazole-derived N-heterocyclic carbenes and their application in gold catalysis

Jin Zhang, Ting Liu, Gaopeng Zhang, Jianglong Cai, Yue Wang, Jianbo Tong, Yangmin Ma, Roman Szostak, Michal Szostak

Research output: Contribution to journalArticlepeer-review

Abstract

Sterically-hindered N-heterocyclic carbenes (NHCs) with functionalized N-wingtips are a pivotal class of ligands in organic synthesis. Herein, we report the first class of sterically-hindered N-heterocyclic carbenes based on the indazole framework. These ligands combine the strong σ-donation of the carbene center due to the carbene placement at the C3-indazole position with the sterically-hindered and flexible N-substitution with the versatile 2,6-bis(diphenylmethyl)aryl moiety that extends beyond the metal centre for the first time in non-classical N-heterocyclic carbenes. The ligands are readily accessible by the rare Cadogan indazole synthesis of sterically-hindered N-aryl-1-(2-nitrophenyl)methanimines. Steric and electronic characterization as well as catalytic studies in the synthesis of oxazolines are described. Considering the unique properties of indazole-derived carbenes, we anticipate that this class of compounds will find broad application in organic synthesis and catalysis.

Original languageEnglish (US)
Pages (from-to)4260-4265
Number of pages6
JournalDalton Transactions
Volume53
Issue number9
DOIs
StatePublished - Feb 1 2024
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Inorganic Chemistry

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