ArticleChemical science2017
Suzuki-Miyaura cross-coupling of amides and esters at room temperature: correlation with barriers to rotation around C-N and C-O bonds.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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Who cites it
36 citing papers in PubMed.
- Pd(II)-NHC (NHC = N-Heterocyclic Carbene)-Catalyzed Alkylation of Primary Amides by Site-Selective N─C(O) Activation.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Gold(I) Complexes of ImPyDippDipp and ImPyMesMes: Biaryl L‑Shaped N‑Heterocyclic Carbene Analogues of IPr and IMes.Organometallics · 2025Article
- Mechanistic insights on C(acyl)-N functionalisation mediated by late transition metals.Dalton transactions (Cambridge, England : 2003) · 2024Review
- IPrOrganometallics · 2024Article
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- [IPrMolecules (Basel, Switzerland) · 2023Article
- IChemical science · 2023Article
- L-Shaped Heterobidentate Imidazo[1,5-a]pyridin-3-ylidene (N,C)-Ligands for Oxidant-Free AuAngewandte Chemie (International ed. in English) · 2023Article
- Divergent Acyl and Decarbonylative Liebeskind-Srogl Cross-Coupling of Thioesters by Cu-Cofactor and Pd-NHC (NHC = N-Heterocyclic Carbene) Catalysis.ACS catalysis · 2023Article
- Amide N-C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling.SynOpen (2017) · 2023Article
- Well-Defined, Air- and Moisture-Stable Palladium-Imidazo[1,5-Catalysis science & technology · 2022Article
- [Ni(Np#)(η5-Cp)Cl]: Flexible, Sterically Bulky, Well-Defined, Highly Reactive Complex for Nickel-Catalyzed Cross-Coupling.Organometallics · 2022Article
- Fe(iii)-catalysed selective C-N bond cleavage ofRSC advances · 2022Article
- Direct Dehydrogenative Access to Unsymmetrical Phenones.Angewandte Chemie (International ed. in English) · 2022Article
- Thiazol-2-ylidenes as N-Heterocyclic carbene ligands with enhanced electrophilicity for transition metal catalysis.Communications chemistry · 2022Article
- Bispidine Platform as a Tool for Studying Amide Configuration Stability.Molecules (Basel, Switzerland) · 2022Article
- [(NHC)PdClThe Journal of organic chemistry · 2021Article
- Mechanistic Aspects of the Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- IPr# - highly hindered, broadly applicable N-heterocyclic carbenes.Chemical science · 2021Article
- Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki-Miyaura Reactions of Diarylmethyl Esters.Organometallics · 2021Article
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Authors and funding
7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The Suzuki-Miyaura cross-coupling has been widely recognized as one of the most important methods for the construction of C-C bonds. However, in contrast to traditional aryl halide or pseudohalide electrophiles, coupling reactions with unactivated C-N and C-O electrophiles have proven significantly more challenging. Here we report the first general palladium-catalyzed Suzuki-Miyaura cross-coupling of both common amides and aryl esters through the selective cleavage of the C-N and C-O bonds under exceedingly mild conditions. Notably, for the first time we demonstrate selective C(acyl)-N and C(acyl)-O cleavage/cross-coupling under the same reaction conditions. The reaction uses a commercially available, bench-stable and operationally-convenient (η
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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.