Issue 97, 2022

CAAC–IPr*: easily accessible, highly sterically-hindered cyclic (alkyl)(amino)carbenes

Abstract

IPr* (IPr* = 1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazol-2-ylidene) has emerged as a powerful highly hindered and sterically-flexible ligand platform for transition-metal catalysis. CAACs (CAAC = cyclic (al-kyl)(amino)carbenes) have gained major attention as strongly electron-rich carbon analogues of NHCs (NHC = N-heterocyclic carbene) with broad applications in both industry and academia. Herein, we report a merger of CAAC ligands with highly-hindered IPr*. The efficient synthesis, electronic characterization and application in model Cu-catalyzed hydroboration of alkynes is described. The ligands are strongly electron-rich, bulky and flexible around the N-Ar wingtip. The availability of various IPr* and CAAC templates offers a significant potential to expand the existing arsenal of NHC ligands to electron-rich bulky architectures with critical applications in metal stabilization and catalysis.

Graphical abstract: CAAC–IPr*: easily accessible, highly sterically-hindered cyclic (alkyl)(amino)carbenes

Supplementary files

Article information

Article type
Communication
Submitted
18 Oct 2022
Accepted
03 Nov 2022
First published
04 Nov 2022

Chem. Commun., 2022,58, 13467-13470

Author version available

CAAC–IPr*: easily accessible, highly sterically-hindered cyclic (alkyl)(amino)carbenes

W. Chu, T. Zhou, E. Bisz, B. Dziuk, R. Lalancette, R. Szostak and M. Szostak, Chem. Commun., 2022, 58, 13467 DOI: 10.1039/D2CC05668B

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