ArticleChemical science2021
IPr# - highly hindered, broadly applicable N-heterocyclic carbenes.
Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed.
- Twisted amide Xantphos ligands: wide bite angle, twist-controlled diphosphines.Chemical communications (Cambridge, England) · 2026Article
- Mechanochemically assembled organometallic complexes: a mechanistic study.Chemical science · 2026Article
- Reversible C─H Insertion in Bulky Unsaturated NHCs: A Carbon-Based Analogue of Oxidative Addition/Reductive Elimination.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Article
- Diversification of Pharmaceuticals via Late-Stage Hydrazination.ACS catalysis · 2025Article
- IPr**Organometallics · 2025Article
- ROMP and Vinyl Polynorbornenes with Vanadium(III) and Nickel(II) diNHC Complexes.International journal of molecular sciences · 2025Article
- Metal-N-Heterocyclic Carbene Complexes in Buchwald-Hartwig Amination Reactions.Chemical reviews · 2025Review
- Gold(I) Complexes of ImPyDippDipp and ImPyMesMes: Biaryl L‑Shaped N‑Heterocyclic Carbene Analogues of IPr and IMes.Organometallics · 2025Article
- The influential IPr: 25 years after its discovery.Chemical science · 2025Review
- IBzH (IBenzhydryl): Sterically-FlexibleCatalysis science & technology · 2024Article
- IPr*Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- IPrOrganometallics · 2024Article
- Wingtip-Flexible N-Heterocyclic Carbenes: Unsymmetrical Connection between IMes and IPr.Angewandte Chemie (International ed. in English) · 2024Article
- Bulky, electron-rich, renewable: analogues of Beller's phosphine for cross-couplings.Catalysis science & technology · 2023Article
- [Au(NpCatalysis science & technology · 2023Article
- Article
- [IPrMolecules (Basel, Switzerland) · 2023Article
- (CAAC)Pd(py) Catalysts Disproportionate to Pd(CAAC)Organometallics · 2023Article
- IChemical science · 2023Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
IPr (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) represents the most important NHC (NHC = N-heterocyclic carbene) ligand throughout the field of homogeneous catalysis. Herein, we report the synthesis, catalytic activity, and full structural and electronic characterization of novel, sterically-bulky, easily-accessible NHC ligands based on the hash peralkylation concept, including IPr#, Np# and BIAN-IPr#. The new ligands have been commercialized in collaboration with Millipore Sigma: IPr#HCl, 915653; Np#HCl; 915912; BIAN-IPr#HCl, 916420, enabling broad access of the academic and industrial researchers to new ligands for reaction optimization and screening. In particular, the synthesis of IPr# hinges upon cost-effective, modular alkylation of aniline, an industrial chemical that is available in bulk. The generality of this approach in ligand design is demonstrated through facile synthesis of BIAN-IPr# and Np#, two ligands that differ in steric properties and N-wingtip arrangement. The broad activity in various cross-coupling reactions in an array of N-C, O-C, C-Cl, C-Br, C-S and C-H bond cross-couplings is demonstrated. The evaluation of steric, electron-donating and π-accepting properties as well as coordination chemistry to Au(i), Rh(i) and Pd(ii) is presented. Given the tremendous importance of NHC ligands in homogenous catalysis, we expect that this new class of NHCs will find rapid and widespread application.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.