398142-11-5

Upstream product

• 3984-34-7 4-(4-chlorophenyl)-4-oxobutanoic acid 
• 7148-01-8 methyl 4-(4-chlorophenyl)-4-oxobutanoate 
• 108-90-7 chlorobenzene 
• 194805-62-4 methyl-4-bromo-pent-4-enoate 
• 118453-36-4 dimethyl 2-(2'-bromoallyl)malonate 
• 35804-44-5 ethyl 4-bromo-4-pentenoate 
• 92975-38-7 4-bromo-4-pentenoic acid tert-butyl ester 
• 1679-18-1 4-Chlorophenylboronic acid 
• 1779-49-3 Methyltriphenylphosphonium bromide 

Downstream Products

• 1537898-05-7 5-(2,2,2-trifluoroethyl)-5-(p-chlorophenyl)dihydrofuran-2(3H)-one 
• 1359975-46-4 2-(4-chlorophenyl)-2-methyl-tetrahydrofuran 
• 127590-48-1 1-(4-chlorophenyl)-4-hydroxy-1-butan-1-one 
• 89058-34-4 4-(4-chlorophenyl)pent-4-enal 

Relevant academic research and scientific papers

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

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.).

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.

Enantioselective Organocatalyzed Bromolactonizations: Applications in Natural Product Synthesis

Asymmetric bromolactonization reactions of δ-unsaturated carboxylic acids have been investigated in the presence of 10 chiral squaramide hydrogen-bonding organocatalysts. The best catalyst enabled the cyclization of several 5-arylhex-5-enoic acids into th

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.

CuX2-mediated oxybromination/aminochlorination of unsaturated amides: Synthesis of iminolactones and lactams

We report herein a CuX2-mediated halocyclization of γ,δ-unsaturated amides for the synthesis of functionalized iminolactones and lactams respectively under mild reaction conditions. Mechanism studies indicated that N-attack cyclization was via a radical route while oxycyclization was via a nucleophilic attack on the activated CC bond.

Asymmetric iodolactonization utilizing chiral squaramides

Asymmetric iodolactonization of γ- and δ-unsaturated carboxylic acids has been explored in the presence of six different chiral organocatalysts 5-8. The catalyst 6b was found to facilitate the cyclization of 5-arylhex-5-enoic acids 1 to the corresponding