Journal Article10.1007/S10562-021-03654-0
Glucopyranoside-Functionalized NHCs-Pd(II)-PEPPSI Complexes: Anomeric Isomerism Controlled and Catalytic Activity in Aqueous Suzuki Reaction
10
TL;DR: In this article, the first system controlled anomeric isomerism of glucopyranoside-functionalized N-heterocyclic carbenes based pyridine enhanced precatalyst preparation, stabilization and initiation type palladium(II) complexes (Glu-NHCs-Pd(II)-PEPPSI, 2a-d) were prepared and fully characterized.
read more
Abstract: The first system controlled anomeric isomerism of glucopyranoside-functionalized N-heterocyclic carbenes based pyridine enhanced precatalyst preparation, stabilization and initiation type palladium(II) complexes (Glu-NHCs-Pd(II)-PEPPSI, 2a–d) were prepared and fully characterized. It is interesting to note that pure β–anomer PEPPSI complex 2d was obtained, in which the Glu-substituent connects to the imidazole heterocycle ring N through ethoxy bridged anomeric carbon. In addition, the catalytic activities revealed that Glu-NHCs-Pd(II)-PEPPSI complexes 2a-d are efficient catalysts for the aqueous Suzuki reaction. Under optimized conditions, a series of fluorene-cored functional materials with different aryl-substituents were synthesized through the Suzuki reaction with excellent yields. The Glu-NHCs-Pd(II)-PEPPSI complex containing bulky and rigid 2,5-dimethylphenyl group played an important role in maintaining the β conformation and improving the catalytic activity significantly.
read more
Chat with Paper
AI Agents for this Paper
Find similar papers on Google Scholar, PubMed and Arxiv
Write a critical review of this paper
Analyze citations of this paper to find unaddressed research gaps
Citations
Carbohydrate-based N-heterocyclic Carbene-Metal Complexes: A New Avenue for Sustainable Catalyst in Organic Transformations
TL;DR: N-heterocyclic carbene (NHC) and their metal complexes have been employed as a catalyst in organic transformations due to its high efficiency, cost-effectiveness, and extraordinary performance as mentioned in this paper .
5
Rational design of galactopyranoside-substituted N-heterocyclic carbene palladium(ii) complexes. Stable and efficient catalyst for C–C coupling in aqueous media
TL;DR: The rational design of galactopyranoside-substituted N-heterocyclic carbene palladium(ii) complexes leads to stable and efficient catalysts for C–C coupling in aqueous media.
3
Synthesis of glucopyranoside benzimidazolium-based ionic liquids for Pd-catalyzed aqueous Suzuki reaction
TL;DR: In this article , several benzimidazolium-based ionic liquids (BzIm ILs) with free and acetyl protected glucopyranoside unit were synthesized and used as ligand for Pd-catalyzed environment-friendly Suzuki reaction.
2
Unexpectedly Superior Efficiency of Chloride-directed Double Suzuki-Miyaura Cross-coupling Reaction to That of Bromide for the Synthesis of Sterically Hindered 2,7-Diaryl Fluorenes
Yuqing Peng,Yongqing Li,maomao liu,Chen Ni,Yucai Cao +4 more
TL;DR: Double Suzuki-Miyaura cross-coupling reaction is unexpectedly more efficient than bromide-directed reaction for the synthesis of sterically hindered 2,7-diaryl fluorenes.
1
New sugar-incorporated N-heterocyclic carbene precursors and their Ag(I) and Pd(II) complexes: Synthesis, characterization, and cytotoxicity studies
Tammar Hussain Ali,Abbas Washeel Salman,Ruqaya Sabah Abdulhussein,Leentje Persoons,Dirk Daelemans,Wim Dehaen,Luc Van Meervelt +6 more
TL;DR: New sugar-incorporated N-heterocyclic carbene precursors and their Ag(I) and Pd(II) complexes were synthesized and characterized. Pd(II) complex 11c exhibited broad anticancer activity against eight diverse cancer cell lines, albeit at higher concentrations than reference drugs.
1
References
Stable abnormal N-heterocyclic carbenes and their applications.
TL;DR: A review article summarizes the results obtained with the isolated aNHCs, which successfully accomplished the metal-free catalytic formylation of amides using CO2 and the catalytic reduction of carbon dioxide, including atmospheric CO2, into methanol, under ambient conditions.
238
Thermodynamics of N-heterocyclic Carbene Dimerization: The Balance of Sterics and Electronics
Albert Poater,Francesco Ragone,Simona Giudice,Chiara Costabile,Reto Dorta,Steven Nolan,Luigi Cavallo +6 more
TL;DR: In this paper, N-heterocyclic carbenes (NHCs) have been used as an alternative to tertiary phosphines as ancillary ligands in catalysis.
234
Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective.
TL;DR: This review intends to present a synthetic toolkit for the immobilization of N-heterocyclic carbene compounds, giving the reader an overview on synthetic techniques and strategies available in the literature.
225
A Bulky Chiral N-Heterocyclic Carbene Palladium Catalyst Enables Highly Enantioselective Suzuki–Miyaura Cross-Coupling Reactions for the Synthesis of Biaryl Atropisomers
TL;DR: The protocol provided general and efficient access to various atropisomeric biaryls and heterobiaryls in excellent enantioselectivities with no need of using bulky ortho-substituted substrates and was effective for the synthesis of tetra-ortho- substituentBiaryls.
215
Postsynthetic Metalation of a Robust Hydrogen-Bonded Organic Framework for Heterogeneous Catalysis.
TL;DR: By simple recrystallization, the catalytic activity of deactivated species can be recovered from the isolation yield 46% to 92% for 4-bromobenzonitrile conversion at the same conditions, revealing the great application potentials of HOF-based catalysts.