53774-21-3

Upstream product

• 127-66-2 2-Phenyl-3-butyn-2-ol 
• 201230-82-2 carbon monoxide 
• 60935-21-9 cyclopropenone-1,3-propanediolketal 
• 98-86-2 acetophenone 
• 98761-44-5 4-Bromo-5-methyl-5-phenyl-5H-furan-2-one 
• 251301-56-1 2-methyl-2-phenyl-2,5-dihydrofuran 
• 246862-25-9 (S)-2-(4-methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)ethyl 2,4,6-triisopropylphenyl sulfoxide 
• 1027560-55-9 5-methyl-5-phenyl-2,5-dihydro-furan-2-yl hydroperoxide 
• 6712-35-2 2-phenylpent-4-yn-2-ol 
• 6051-52-1 2-phenylbut-3-en-2-ol 
• 1061364-58-6 dihydro-5-methyl-5-phenyl-4-(phenylselenyl)furan-2(3H)-one 
• 223243-86-5 (E)-4-phenyl-3-pentenoic acid 
• 108-86-1 bromobenzene 
• 61550-05-8 trimethyl-(5-methyl-furan-2-yloxy)-silane 

Downstream Products

• 67545-33-9 (Z)-5-Methyl-2-phenylhexen-3-diol-2,5 
• 20731-95-7 methyl 2-hydroxy-2-phenylpropanoate 

Relevant academic research and scientific papers

Electrochemical oxidative bromolactonization of unsaturated carboxylic acids with sodium bromide: Synthesis of bromomethylated γ-lactones

Electrochemical oxidative bromination and cyclization sequences of unsaturated carboxylic acids were developed in this study. This approach is environmentally-friendly, using bromide anion as bromine radical precursor without external oxidizing reagents.

A facile synthesis of γ-butenolides via cyclization of 3-alkenoic acids with dimethyl sulfoxide and oxalyl bromide

The combination of dimethyl sulfoxide and oxalyl bromide was used to accomplish the cyclization of 3-alkenoic acids with the aid of a base to afford γ-butenolides, in which bromodimethylsulfonium salt generated in situ was proposed to serve as a Br+ source.

Comparative studies of palladium and copper-catalysed γ-arylation of silyloxy furans with diaryliodonium salts

The γ-arylation of substituted silyl-activated butenolides has been studied using a broad scope of unsymmetrical hypervalent diaryliodonium salts via a palladium- or copper-catalysed coupling reaction, yielding interesting reactivity trends. The mild catalytic conditions and coupling partner variability provide access to synthetically useful building blocks toward the pursuit of aryl-lactone containing natural products and allows for facile diversification.

Guiding a divergent reaction by photochemical control: Bichromatic selective access to levulinates and butenolides

Allylic and acrylic substrates may be efficiently transformed by a sequential bichromatic photochemical process into derivatives of levulinates or butenolides with high selectivity when phenanthrene is used as a regulator. Thus, UV-A photoinduced cross-metathesis (CM) couples the acrylic and allylic counterparts and subsequent UV-C irradiation initiates E-Z isomerization of the carbon-carbon double bond, followed by one of two competing processes; namely, cyclization by transesterification or a 1,5-H shift and tautomerization. Quantum chemical calculations demonstrate that intermediates are strongly blue-shifted for the cyclization while red-shifted for the 1,5-H shift reaction. Hence, delaying the double bond migration by employing UV-C absorbing phenanthrene, results in a selective novel divergent all-photochemical pathway for the synthesis of fundamental structural motifs of ubiquitous natural products.

Activation of the hypervalent fluoroiodane reagent by hydrogen bonding to hexafluoroisopropanol

Hexafluoroisopropan-2-ol (HFIP) is an excellent solvent for promoting fluorinations with the hypervalent fluoroiodane reagent 1 and crucially, it removes the need for transition metals or TREAT-HF activators. The fluoroiodane reagent 1 was used in HFIP to monofluorinate 1,3-ketoesters and to fluorocyclise unsaturated carboxylic acids in excellent yields under mild reaction conditions.

Convenient synthesis of α,β-unsaturated γ-butyrolactones and γ-butyrolactams via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams using 1,3-diiodo-5,5-dimethylhydantoin

A convenient synthetic approach to α,β-unsaturated γ-butyrolactones and α,β-unsaturated γ-butyrolactams is developed. The reaction proceeds via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams, employing 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation, followed by dehydroiodination of β-iodo-γ-butyrolactones and γ-butyrolactams providing good yields of α,β-unsaturated γ-butyrolactones and γ-butyrolactams, which are synthetically useful building blocks in organic synthesis.

Indole-Catalyzed Bromolactonization in Lipophilic Solvent: A Solid-Liquid Phase Transfer Approach

We have developed a novel indole-catalyzed bromolactonization of olefinic acids. The reaction could be conducted in lipophilic solvent through a solid-liquid phase transfer mechanism. This catalytic protocol has been applied to the synthesis of base-sensitive bromolactones. (Chemical Equation Presented).

Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones

The transformation of cyclic hemiacetals (lactols) into lactones has been achieved by Cu-catalyzed aerobic C-C bond cleavage in the presence of N-hydroxy phthalimide (NHPI). The present process is composed of a multistep sequence including a) formation of exo-cyclic enol ethers by dehydration; b) addition of phthalimide N-oxyl radical to the enol ethers followed by trapping of the resulting C-radicals with molecular oxygen to form peroxy radicals; c) reductive generation of oxy radicals and subsequent β-radical fragmentation to generate lactones.

Palladium-catalyzed asymmetric intermolecular Mizoroki-Heck reaction for construction of a chiral quaternary carbon center

Palladium-catalyzed asymmetric intermolecular Mizoroki-Heck reaction for the construction of a chiral quaternary carbon center is developed, affording 2,2-disubstituted 2,5-dihydrofurans in high yield with excellent enantioselectivity. The products are ea

Synthesis of chiral butenolides using amino-thiocarbamate-catalyzed asymmetric bromolactonization

The asymmetric cyclization of 4,4-disubstituted 3-butenoic acids is studied. Amino-thiocarbamates are used as the catalysts and N-bromosuccinimide is used as the stoichiometric halogen source. The resulting γ-butanolide products are readily converted into the corresponding γ-butenolides (up to 58% ee) derivatives in one-pot.