A5077476752- Catalytic C–H Functionalization Methods
- Catalytic Cross-Coupling Reactions
- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Organometallic Complex Synthesis and Catalysis
- Carbon dioxide utilization in catalysis
- biodegradable polymer synthesis and properties
- Coordination Chemistry and Organometallics
- Asymmetric Hydrogenation and Catalysis
- Sulfur-Based Synthesis Techniques
- Fluorine in Organic Chemistry
- Synthesis and Catalytic Reactions
- Cyclopropane Reaction Mechanisms
- Radical Photochemical Reactions
- Asymmetric Synthesis and Catalysis
- Synthesis and characterization of novel inorganic/organometallic compounds
- Organoboron and organosilicon chemistry
- Chemical Synthesis and Analysis
- Catalytic Alkyne Reactions
- Chemical synthesis and alkaloids
- Click Chemistry and Applications
- Synthetic Organic Chemistry Methods
- Synthesis of heterocyclic compounds
- Crystallography and molecular interactions
- N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
University of Science and Technology of China
2016-2025
Yancheng Institute of Technology
2024
Collaborative Innovation Center of Chemical Science and Engineering Tianjin
2015-2022
Hefei University
2015-2021
State Council of the People's Republic of China
2017-2019
Hefei National Center for Physical Sciences at Nanoscale
2017-2018
Microscale (United States)
2017-2018
State Key Laboratory of Synthetic Chemistry
2011
University of Sussex
2008
Broad scope and good tolerance: An efficient cross-coupling of aryltrimethylammonium iodide salts with aryl-, methyl-, benzylzinc chlorides catalyzed by [Ni(PCy3)2Cl2] has been achieved (see scheme). The reaction involves cleavage the CN bond displays broad substrate functional group tolerance. NMP=N-methylpyrrolidine. Detailed facts importance to specialist readers are published as ”Supporting Information”. Such documents peer-reviewed, but not copy-edited or typeset. They made available...
Solventless condensation of a diketone and hydrazine in the presence catalytic amount sulfuric acid at room temperature afforded pyrazole derivatives 3a–3i 4g–4i high yields. The 2,4-pentanedione hydrazides gave similar results, while reaction between 1-phenylbutane-1,3-dione under same conditions 4,5-dihydro-5-hydroxypyrazole 6a 6b, which can be transformed to 4i (for 6b) or mixture 1-acylpyrazole 3i (4i) 6a) by thermolysis acid. Similar ethyl acetoacetate with phenylhydrazine formed...
N-Heterocyclic carbene-based pincer nickel complexes were synthesized and characterized. These efficiently catalyze cross-coupling of aryl Grignard reagents with chlorides or fluorides under mild conditions.
Abstract Transition‐metal‐catalyzed cross‐coupling reactions are powerful tools for constructing carbon–carbon and carbon–heteroatom bonds. In this microreview we summarize the nickel‐catalyzed with pincer ligands. The presented here include Kumada, Negishi, Suzuki, Sonogashira formation of different types C–C bonds, as well thiolation aryl iodides.
The cross-coupling reaction of aryltrimethylammonium iodides with aryl- or heteroarylzinc chlorides catalyzed by amido pincer nickel complexes was performed. requires low catalyst loading and displays broad substrate scope.
Ni(PCy3)2Cl2 was demonstrated to effectively catalyze cross-coupling of aryl fluorides and organozinc reagents. Both electron-poor -rich can react with nucleophiles including aryl-, methyl-, benzylzinc chlorides. A wide range substituents functional groups are tolerated. In the presence a directing group, PhC(O), reaction is selective for cleavage C–F bond ortho carbonyl substituent in difluoroarene.
The reaction of quaternary ammonium salts <italic>via</italic> C–N bond cleavage to construct C–C, C–H and C–heteroatom bonds is summarized.
A series of aluminum and zinc complexes supported by pyridine-based N,N,N-chelate ligands have been synthesized characterized. Treatment 2-(3,5-dimethyl-1H-pyrazol-1-yl)-6-((trimethylsilyl)methyl)pyridine (2) with LiBun/tmeda then PhCN afforded a lithium complex [Li{2-(3,5-Me2C3HN2)-6-{N(SiMe3)C(Ph)═CH}C5H3N}] ([LiL]) (3). Reaction 3 ZnCl2 formed corresponding chloride [Zn(Cl)L] (4), which was transformed to methyl- or ethylzinc [Zn(R)L] (R = Me, 5a; R Et, 5b) treatment ethyllithium. The...
The synthesis and characterization of N,N,O-chelate zinc enolate complexes the catalysis for ROP rac-lactide are reported. pyrazole-based ligand precursors o-(3,5-Me2C3HN2)C6H4N═C(Me)CH═C(OH)R1 (R1 = Me, 1; R1 Ph, 2; t-Bu, 3; CF3, 4)were synthesized by reaction 2-(3,5-dimethyl-1H-pyrazol-1-yl)benzenamine with 1,3-diketones, including pentane-2,4-dione,1-phenylbutane-1,3-dione, 5,5-dimethylhexane-2,4-dione, 1,1,1-trifluoropentane-2,4-dione. Treatment 1–4 ZnEt2 generated N,N,O-coordinated...
A series of zinc and aluminum complexes supported by quinoline-based N,N,N-chelate ligands were synthesized characterized. The reaction 2-PyCH2PPh2 or ArN═C(Ph)CH2PPh2 (Ar = Ph, p-MeC6H4, p-MeOC6H4) with 8-azidoquinoline in dichloromethane gave the iminophosphoranes 2-PyCH2P(Ph2)═N(8-C8H6N) (1; C8H6N quinolyl) ArN═C(Ph)CH2P(Ph2)═N(8-C8H6N), respectively. Treatment 1 equiv ZnEt2 afforded corresponding [Zn(Et){2-PyCHP(Ph2)═N(8-C8H6N)}] (2) [Zn(Et){ArNC(Ph)═CHP(Ph2)═N(8-C8H6N)}] (5a, Ar Ph; 5b,...
Nickel-catalyzed cross-coupling of aryltrimethylammonium triflates and amines was carried out under mild conditions. The reaction has a broad scope substrates can be performed by one-pot procedure from an aryldimethylamine.
Synthesis and characterization of novel dinuclear magnesium, zinc aluminum complexes supported by bis(iminopyrrolide) ligands their catalysis toward the ring-opening polymerization (ROP) ε-caprolactone (ε-CL) rac-lactide (rac-LA) were carried out. The ligand precursors [(5-But-2-C4H2NH)CHN(CH2)2]2NH (H2LBu, 1) [(2-C4H3NH)CHN(CH2)2]2NH (H2LH, 2) prepared condensation diethylene triamine with 5-tert-butyl-1H-pyrrole-2-carbaldehyde 1H-pyrrole-2-carbaldehyde, respectively. Treatment 1 2 equiv....
An Ru-catalyzed carbamoyl-directed C–H functionalization of indoles and indolines with 7-azabenzonorbornadienes results in 2-aminodihydronaphthyl 7-aminodihydronaphthyl indolines, respectively.
The nickel-catalyzed reaction of benzocyclic quaternary ammonium salts with arylzinc reagents or arylboron affords amino-retentive arylation products in 40%-95% yields. protocol suits for various substituted ammonium...
Novel nickel complexes bearing P,N,P-, P,N,N- and N,N,N- amido pincer ligands exhibited highly catalytic activity in Kumada coupling reactions.
Two C,N,N-chelate nickel complexes, [Ni(Cl){2-(CN(Me)(CH)2N)C6H4N═P(Ph2)CH2Pyr}]+I− and [Ni(Cl){2-(CN(Pri)(CH)2N)C6H4N═P(Ph2)CH2P(Ph2)═NC6H4Me-4}]+I−, were synthesized by reaction of (DME)NiCl2 (DME = 1,2-dimethoxyethane) with 2-(CN(R)(CH)2N)C6H4N═P(Ph2)CH2Z (R Me, Z 2-Pyr; R Pri, p-MeC6H4N═P(Ph2)) ligands, which prepared in situ corresponding imidazolium salts 1 equiv LiBun. C,N,P-Chelate complex [Ni(Br){2-(CN(CH2Ph)(CH)2N)C6H4N═P(Ph2)CH2PPh2}]+Br− was obtained a similar between (DME)NiBr2...
A series of amido pincer complexes nickel were examined for their catalysis in the Kumada cross-coupling reaction. The P,N,O-pincer tested are active catalysts aryl, heteroaryl, and vinyl chlorides with aryl Grignard reagents. reactions can proceed at room temperature tolerate functional groups aid LiCl ZnCl(2) additives.
Two series of ligand precursors [2-OH-3-(CH(2)NR(2))-5-MeC(6)H(2)](2)CH(2) (1: NR(2) = NMe(2); 2: N(CH(2))(4); 3: N(CH(2))(5); 4: N(Me)Ph) and [2-OH-3-(CH=NR)-5-MeC(6)H(2)](2)CH(2) (10: R 2,6-Pr(2)(i)C(6)H(3); 11: p-MeC(6)H(4); 12: p-ClC(6)H(4); 13: p-MeOC(6)H(4); 14: Bu(t)) were prepared. These compounds reacted with AlMe(3) to afford corresponding dinuclear aluminum complexes [AlMe(2){2-O-3-(CH(2)NR(2))-5-MeC(6)H(2)}](2)CH(2) (6: 7: 8: 9: [AlMe(2){2-O-3-(CH=NR)-5-MeC(6)H(2)}](2)CH(2) (15:...
The synthesis and catalysis in the ring-opening polymerisation (ROP) of ε-caprolactone (ε-CL) aluminium(III) tin(II) complexes supported by quinoline-based N,N,O-tridentate ligands are reported. Reaction 8-{RC(O)CH2P(Ph2)N}C9H6N (R = But, 2; R Ph, 3) with AlMe3 gave [Al(Me2){OCRCHP(Ph2)N(8-C9H6N)}] 4; 5). Treatment 2 3 Sn[N(SiMe3)2]2 generated [Sn{OC(R)CHP(Ph2)N(8-C9H6N)}{N(SiMe3)2}] 6; 7). A similar reaction 8-{MeC(O)CH2C(Me)N}C9H6N [Al(Me2){OC(Me)CHC(Me)NC9H6N}] (9). Compounds 2–9 were...
Nickel-catalyzed cross-coupling of allyl alcohols with aryl- and alkenylzinc chlorides through C-O bond cleavage was performed. Reaction (E)-3-phenylprop-2-en-1-ol 1-aryl-prop-2-en-1-ols or gave linear products. 1-phenyl- 1-methyl-substituted resulted in 3-aryl/alkenyl-substituted (E)-(prop-1-ene-1,3-diyl)dibenzenes (E)-(but-1-enyl)benzene. alcohol p-Me2NC6H4ZnCl a mixture normal coupling product 4-allyl-N,N-dimethylaniline its isomerized N,N-dimethyl-4-(prop-1-en-1-yl)aniline.
<italic>N</italic>,<italic>N</italic>,<italic>P</italic>-Pincer nickel complexes [Ni(Cl){N(2-R<sub>2</sub>PC<sub>6</sub>H<sub>4</sub>)(2′-Me<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>)}] highly effectively catalyze the cross-coupling of aryltrimethylammonium triflates with arylzinc reagents.
A methodology that allows for the construction of C-P bonds via nickel-catalyzed cross-coupling organoammonium salts with appropriate phosphorus nucleophiles has been developed. Aryl-, pyridyl-, benzyl-, and allyl-ammonium triflates can be employed as electrophiles. The phosphorus-based included diaryl/dibutyl phosphine oxide, dialkyl phosphonates, ethyl phenylphosphinate. Functional groups OMe, CN, CF3, F, Cl, C(O)NMe2, C(O) tBu were tolerated.
Abstract Treatment of 1‐(2′‐azidophenyl)‐3,5‐dimethylpyrazole ( 1 ) with Ph 2 PR (R = Ph, Me) and (Ph P) CH , respectively, affords the pyrazolyliminophosphoranes 3 4 . Reaction or [NiCl (dme)] NiBr yields N,N‐chelate nickel complexes 5 – 8 CoCl 9 10 (dme)], N,N,P‐chelate 11 13 Compounds were characterised by H, C, 31 P NMR IR spectroscopy elemental analysis, while analysis. The structures 12 further single‐crystal X‐ray diffraction techniques. Complexes are active catalysts for ethylene...