18476-65-8

Upstream product

• 19082-37-2 1-hydroxy-1-phenyl-4-pentyne 
• 106-96-7 propargyl bromide 
• 98-86-2 acetophenone 
• 13466-32-5 acetophenone dimethylhydrazone 
• 100-52-7 benzaldehyde 
• 5390-04-5 pent-1-yn-5-ol 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 79-37-8 oxalyl dichloride 
• 100-58-3 phenylmagnesium bromide 
• 152705-37-8 N-methoxy-N-methylpent-4-ynamide 
• 6089-09-4 4-pentynoic acid 

Downstream Products

• 126594-10-3 2-(hydroxy-1-phenyl-4-pentynyl)-1,3-dithiane 
• 73881-02-4 1-Phenyl-1,4,6-heptantrion 
• 174873-74-6 N-methyl-1-phenyl-4-pentynylamine 
• 34721-89-6 2-methyl-5-phenyl-furan 
• 583-05-1 1-phenylpentane-1,4-dione 
• 126594-11-4 2-<1-<(trimethylsilyl)oxy>-1-phenyl-4-pentynyl>-1,3-dithiane 
• 1234344-80-9 1-phenylhept-6-en-4-yn-1-one 
• 1322013-10-4 C₁₄H₁₄O 
• 1590431-59-6 6-phenylbicyclo[4.2.0]octa-1,3-diene 
• 1590431-49-4 (1-cyclopropylidenepent-4-yn-1-yl)benzene 
• 3042-21-5 2-methyl-5-phenyl-1H-pyrrole 

Relevant academic research and scientific papers

Dibrominative Spirocyclization of 2-Butynolyl Anilides: Synthesis of gem-Dibromospirocyclic Benzo[ d][1,3]oxazines and Their Application in the Synthesis of 4 H-Furo[3,2- b]indoles

The combination of catalytic aqueous hydrochloric acid (HCl) and N-bromosuccinimide (NBS) generated electrophilic bromine monochloride (BrCl), which readily induced spiroannulation of 2-alkynolyl anilides (n = 1-3) to form gem-dibromospirocyclic benzo[d][

Silver-Catalyzed Oxyphosphorylation of Unactivated Alkynes

Here, we describe an application of hydroazidation in the instant activation of alkynes for achieving the oxyphosphorylation of unactivated alkynes with diarylphosphinoyl radicals under mild reaction conditions. This reaction provides a method for accessing β-ketophosphine oxides and phosphorus-containing pyrroles. (Figure presented.).

Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis

Here we report the first example of alkyne trifunctionalization through simultaneous construction of C-C, C-O, and C-N bonds via gold catalysis. With the assistance of a γ-keto directing group, sequential gold-catalyzed alkyne hydration, vinyl-gold nucleophilic addition, and gold(III) reductive elimination were achieved in one pot. Diazonium salts were identified as both electrophiles (N source) and oxidants (C source). Vinyl-gold(III) intermediates were revealed as effective nucleophiles toward diazonium, facilitating nucleophilic addition and reductive elimination with high efficiency. The rather comprehensive reaction sequence was achieved with excellent yields (up to 95%) and broad scope (>50 examples) under mild conditions (room temperature or 40 °C).

Regioselective Crossed Aldol Reactions under Mild Conditions via Synergistic Gold-Iron Catalysis

A synergistic gold-iron (Au-Fe) catalytic system was developed for sequential alkyne hydration and vinyl Au addition to aldehydes or ketones. Fe(acac)3 was identified as an essential co-catalyst in preventing vinyl Au protodeauration and facilitating nucleophilic additions. Effective C–C bond formation was achieved under mild conditions (room temperature) with excellent regioselectivity and high efficiency (1% [Au], up to 95% yields). The intramolecular reaction was also achieved, giving successful macrocyclization (16–31 ring sizes) with excellent yields (up to 90%, gram scale) without extended dilution (0.2 M), which highlights the great potential of this new crossed aldol strategy in challenging target molecule synthesis. Effective construction of the C–C bond is one of the most important tasks in organic synthesis. Whereas aldol condensation is a classic C–C bond-forming transformation, it requires other chemical promoters, such as strong base and reactive acidic catalysts. As a result, the overall transformation is limited in terms of ideal atom economy and environmentally friendly operation. With the discovery of a gold-iron (Au-Fe) synergistic catalysis system, here we describe a new approach to facilitating alkyne hydration and sequential vinyl Au addition to carbonyls. This approach gives the C–C bond-forming products in excellent yields, wide substrate scope, and great functional-group compatibility under mild conditions. This protocol can also be applied to macrocyclization without extended dilution. This C–C bond-forming strategy could facilitate challenging molecule synthesis in chemical, biological, and medicinal research. We report a synergistic gold-iron (Au-Fe) catalytic system to access vinyl Au reactivity by avoiding frequently occurring protodeauration. Fe(acac)3 was identified as an essential co-catalyst, facilitating vinyl Au addition to aldehydes. A broad substrate scope was obtained under mild conditions (room temperature) with excellent regioselectivity and high efficiency (1% [Au], up to 95% yields). This protocol offers a practical solution for achieving macrocyclization (16–31 ring sizes, up to 90%, gram scale) without extended dilution, highlighting the synthetic utility in complex molecular synthesis.

K2CO3-Mediated Cyclization and Rearrangement of γ,δ-Alkynyl Oximes to Form Pyridols

A novel K2CO3-mediated cyclization and rearrangement of γ,δ-alkynyl oximes for the synthesis of pyridols is described. The process accomplishes an efficient [1,3] rearrangement of the O-vinyl oxime intermediate which is in situ generated from the intramolecular nucleophilic addition of γ,δ-alkynyl oximes. The reaction employs readily accessible starting materials, tolerates a wide range of functional groups, and gives a variety of synthetically challenging pyridols in good yields.

Silver-free activation of ligated gold(I) chlorides: The use of [Me3NB12Cl11]- as a weakly coordinating anion in homogeneous gold catalysis

Phosphane and N-heterocyclic carbene ligated gold(I) chlorides can be effectively activated by Na[Me3NB12Cl11] (1) under silver-free conditions. This activation method with a weakly coordinating closo-dodecaborate anion was shown to be suitable for a large variety of reactions known to be catalyzed by homogeneous gold species, ranging from carbocyclizations to heterocyclizations. Additionally, the capability of 1 in a previously unknown conversion of 5-silyloxy-1,6-allenynes was demonstrated.

Water-soluble aryl-extended calix[4]pyrroles with unperturbed aromatic cavities: synthesis and binding studies

We report the synthesis of a novel, water-soluble aryl-extended calix[4]pyrrole receptor. The water-solubilising groups are placed at the lower rim of the receptor, leaving the binding pocket unperturbed and open for modification. Binding studies were performed with a series of pyridine N-oxides. These studies revealed the ability of the receptor to bind neutral and charged N-oxides in basified water with stability constants higher than 104 M-1.

Gold-catalyzed enantioselective ring-expanding cycloisomerization of cyclopropylidene bearing 1,5-enynes

An enantioselective ring-expanding cycloisomerization of 1,5-enynes bearing a cyclopropylidene moiety has been developed. This methodology provides a new approach to bicyclo[4.2.0]octanes, a structural motif present in many biologically active natural products.

Enantioselective preparation of 8-oxabicyclo[3.2.1]octane derivatives via asymmetric [3+2]-cycloaddition of platinum-containing carbonyl ylides with vinyl ethers

A catalytic asymmetric synthesis of 8-oxabicyclo[3.2.1]octane derivatives was achieved through the [3+2]-cycloaddition of the platinum-containing carbonyl ylides generated from acyclic γ,δ-ynones on treatment with 10 mol % of PtCl2-Walphos and

Stereoselective synthesis of medium-sized cyclic compounds through the intramolecular michael-type reaction utilizing alkyne-hexacarbonyldicobalt complex formation

Alkyne-hexacarbonyldicobalt complexes having silyl enol ether and electron-deficient alkene moieties on opposite ends were treated with MeAlCl2 in the presence of 2,6-di-t-butylpyridine in CH 2Cl2 to give synthetically use