889656-10-4

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 366-77-8 4-(4-fluorophenyl)-4-oxopropionic acid 
• 462-06-6 fluorobenzene 
• 39560-31-1 methyl 3-(4-fluorobenzoyl)-propionate 

Downstream Products

• 889656-11-5 4-(4-fluorophenyl)pent-4-en-1-ol 
• 889656-12-6 4-(4-fluorophenyl)pent-4-enal 
• 889656-05-7 [3-(4-fluorophenyl)but-3-enyl]methylamine 
• 1265529-41-6 5-(chloromethyl)-5-(4-fluorophenyl)dihydrofuran-2(3H)-one 
• 1217263-90-5 5-(chloromethyl)-5-(4-fluorophenyl)dihydrofuran-2(3H)-one 
• 1537898-04-6 5-(2,2,2-trifluoroethyl)-5-(p-fluorophenyl)dihydrofuran-2(3H)-one 

Relevant academic research and scientific papers

Synthesis of Chiral Sulfonyl Lactones via Copper-Catalyzed Asymmetric Radical Reaction of DABCO?(SO2)

In the present work, an asymmetric copper-catalyzed radical multi-component cascade reaction of an unsaturated carboxylic acid, aryldiazonium tetrafluoroborate, and DABCO?(SO2)2 (DABSO) has been developed for the enantioselective synthesis of sulfonyl lactones. In this reaction, this SO2 surrogate, DABSO was applied for the first time in the construction of chiral compounds. This multiple-step asymmetric radical reaction was carried out under mild conditions and tolerated a wide range of substrates, resulting in the corresponding sulfonyl lactones with up to 95% chemical yields and 88% ee. The current reaction enriches the research contents of DABSO, and provides a new and efficient strategy to chiral functionalized lactones bearing quarternary stereogenic center. (Figure presented.).

Synthesis of Novel C 2-Symmetric Sulfur-Based Catalysts: Asymmetric Formation of Halo- and Seleno-Functionalized Normal- and Medium-Sized Rings

The synthesis of novel, highly functionalized, C 2 -symmetric sulfur-based catalysts is developed and their catalytic applications are explored in asymmetric bromo-, iodo- and seleno-functionalizations of alkenoic acids. This protocol provides

Visible-Light-Catalyzed Phosphonation-Annulation: an Efficient Strategy to Synthesize β-Phosphonopyrrolidines and β-Phosphonolactones

A new type of phosphine radical precursor for C—P bond formation has been developed and successfully used in visible-light-catalyzed phosphonation-annulation of unsaturated sulfonamides and carboxylic acids. The catalytic process is simple and green acces

Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents

A versatile synthesis of azidolactones through azidation and cyclization of carboxylic acids onto alkenes has been developed. Based on either photoredox or palladium catalysis, (1,1) and (1,2) azido lactones can be selectively synthesized. The choice of catalyst and benziodoxol(on)e reagent serving as azide source was essential to initiate either a radical or Lewis acid mediated process with divergent outcome. These transformations were carried out under mild conditions using a low catalyst loading and gave access to a large scope of azido lactones.

Photoredox-Catalyzed Cascade Difluoroalkylation and Intramolecular Cyclization for Construction of Fluorinated γ-Butyrolactones

A cascade visible-light photocatalytic difluoroalkylation and intramolecular cyclization reaction has been developed for the synthesis of difluoroalkylated oxygen heterocycles. The reaction was carried out under very mild conditions, affording fluorinated

Cobalt-catalyzed oxidative cyclization of gem-disubstituted conjugated alkenols

Aryl gem-disubstituted conjugated alkenols underwent oxidative cyclization affording 2,5,5-trisubstituted tetrahydrofurans in reasonable yields and good diastereoselectivities using the reductive termination variation of the Mukaiyama aerobic oxidative reaction. Under oxidative termination, the same alkenols produced diols and ketonic by-products via the double hydration and beta-scission competing pathways. Furthermore, the differences in alkenol reactivity under the reductive and oxidative termination conditions were investigated.

Intramolecular fluorocyclizations of unsaturated carboxylic acids with a stable hypervalent fluoroiodane reagent

A new class of fluorinated lactones was prepared by the intramolecular fluorocyclizations of unsaturated carboxylic acids by using the stable fluoroiodane reagent in combination with AgBF4. This unique reaction incorporates a cyclization, an aryl migration, and a fluorination all in one step. The fluoroiodane reagent, prepared easily from fluoride, can also be used without a metal catalyst to give moderate yields within just 1 hour, thus demonstrating that it is a suitable reagent for developing new 18F-labelled radiotracers for PET imaging. All in one: A new class of lactones containing a tertiary alkyl fluoride was prepared in high yields by using a stable fluoroiodane reagent. This unique reaction incorporates a cyclization, an aryl migration, and a fluorination all in one step.

Asymmetric bromolactonization using amino-thiocarbamate catalyst

A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of γ-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.

Rhodium-catalyzed intramolecular, anti-Markovnikov hydroamination. Synthesis of 3-arylpiperidines

The intramolecular anti-Markovnikov hydroamination of 1-(3-aminopropyl)vinylarenes in the presence of a readily available rhodium catalyst to form 3-arylpiperidines is reported. In contrast to intermolecular hydroamination of vinylarenes, which occurred in high yields in the presence of rhodium catalysts containing DPEphos, the intramolecular reaction occurred in high yield in the presence of [Rh(COD)(DPPB)]BF4 as catalyst. Reactants with substituents β to the nitrogen occurred in high yield, and these reactions formed 3,5-disubstituted piperidines with high diastereomeric excess. The regiochemistry of these cyclizations contrasts with the regiochemistry of intramolecular hydroaminations catalyzed by lanthanide complexes, group III metal complexes, and platinum complexes, all of which have been reported to form cyclization products from Markovnikov addition. Copyright