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Relevant academic research and scientific papers

Gold(I) Complexes with Eight-Membered NHC Ligands: Synthesis, Structures and Catalytic Activity

A series of expanded-ring NHC gold complexes of the formula (NaphtDHD?Ar)Au?X (NaphtDHD=4,5-dihydro-1H-naphtho[1,8-ef][1,3]diazocin-3(2H)-ylidene; Ar: Mes=2,4,6-trimethylphenyl, Dipp=2,6-diisopropylphenyl or Xyl=2,6-dimethylphenyl; X=Cl, NCCH3, NTf2) have been synthesized, including the first gold(I) triflimidate complex (5) stabilized by an eight-membered NHC ligand. The new organogold compounds have been characterized by mass spectrometry, IR spectroscopy, and 1H and 13C NMR spectroscopy. The structural geometries of 3 b–c and 5 have been unequivocally established by crystallographic analysis revealing broad N-C-N angles (>121°) and high buried volume values (46–54%). The first catalytic studies were carried out on the cycloisomerization of 1,6-enynes, obtaining full conversions (0.5 mol% catalyst loading) and excellent endo/exo selectivity (up to 99:1), and on the gold-catalyzed phenol synthesis. Lastly, the (NaphtDHD-Dipp)Au+ NTf2? species was subjected to a kinetic experiment in the cyclization of a N-propargyl carboxamide to evaluate the efficiency of the pre-formed catalyst (5) and the in situ activated gold complex (3 b+AgNTf2). (Figure presented.).

Synthesis and Catalytic Applications of Multinuclear Gold(I)-1,2,3-Triazolylidene Complexes

A series of mono- to trinuclear gold(I) complexes (1–3) supported by oxo-functionalized 1,2,3-triazolylidenes have been prepared. All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, elemental analyses, and in the case of complexes 1 and 2 by x-ray diffraction. The catalytic performance of the new triazolylidene gold complexes was tested in several hydroelementation and cyclization processes employing a variety of alkynes as starting materials. According to the overall results, the trinuclear complex 3 displayed the highest catalytic activity in all processes, providing good to excellent yields under mild reaction conditions.

Dual H-bond activation of NHC-Au(i)-Cl complexes with amide functionalized side-arms assisted by H-bond donor substrates or acid additives

Novel approach with amide-tethered H-bond donor NHC ligands enabled Au(i)-catalysis via H-bonding. The plain NHC-Au(i)-Cl complex catalysed conversions of terminal N-propynamides to oxazolines, and enyne cycloisomerization with an acid additive, in DCM at

Fluorocyclization of N-Propargylamides to Oxazoles by Electrochemically Generated ArIF2

A sustainable synthesis of 5-fluoromethyl-2-oxazoles by use of electrochemistry has been demonstrated. Hypervalent ArIF2 is generated by direct electrochemical oxidation of iodoarene ArI in Et3N·5HF and mediates the fluorocyclization

Gold(I) Complexes Stabilized by Nine- and Ten-Membered N-Heterocyclic Carbene Ligands

Nine- and ten-membered N-heterocyclic carbene (NHC) ligands have been developed and for the first time their gold(I) complexes were synthesized. The protonated NHC pro-ligands 2 a–h were prepared by the reaction of readily available N,N′-diarylformamidines with bis-electrophilic building blocks, followed by anion exchange. In situ deprotonation of the tetrafluoroborates 2 a–h with tBuOK in the presence of AuCl(SMe2) provided fast access to NHC-gold(I) complexes 3–10. These new NHC-gold(I) complexes show very good catalytic activity in a cycloisomerization reaction (0.1 mol % catalyst loading, up to 100 % conversion) and their solid-state structures reveal high steric hindrance around the metal atom (%Vbur up to 53.0) which is caused by their expanded-ring architecture.

Assessing the influence of phosphine substituents on the catalytic properties of self-stabilised digold(i) complexes with supporting ferrocene phosphinonitrile ligands

Gold(i) phosphine complexes are often used in catalysis, but the role of their auxiliary ligands still remains poorly understood. Thus, building on our previous research, we prepared a series of Au(i) complexes [Au2(μ-R2PfcCN)2][SbF6]2 (fc = ferrocene-1,1

Synthesis and characterization of a gold(i) bis(triazolylidene) complex featuring a large [(TpMe2)2K] anion

In the quest of heteroleptic gold(i) complexes containing triazolylidenes (MIC) and TpMe2 ligands, we discovered that reaction of the MIC-Au-I complex 2 with potassium hydrotris-(3,5-dimethyl-1-pyrazolil) borate (KTpMe2) produces an

An ambiphilic phosphine/H-bond donor ligand and its application to the gold mediated cyclization of propargylamides

We describe the synthesis of an ambiphilic phosphine/H-bond donor ligand featuring a trifluoroacetamide functionality, its coordination to gold(i) chloride, and its application as a self-activating catalyst for the cyclization of propargylamides.

Tungsten and molybdenum catalyst-mediated cyclisation of N-propargyl amides

Tungsten and molybdenum catalysts were employed to promote the cyclisation of N-propargylic amides to afford the corresponding oxazolines or oxazines via 5-exo-dig or 6-endo-dig mode.