35660-91-4

Upstream product

• 52755-38-1 1-phenyl-2-buten-1-ol 
• 73922-81-3 4-phenyl-but-3-yn-2-ol 
• 66680-84-0 (Z)-1-propenyltributyltin 
• 98-88-4 benzoyl chloride 
• 75-07-0 acetaldehyde 
• 70-11-1 α-bromoacetophenone 
• 25726-04-9 phenylglyoxylyl chloride 
• 24850-33-7 allyltributylstanane 
• 6249-80-5 1-phenylbut-3-en-1-one 
• 57204-89-4 α-(phenylseleno)butyrophenone 
• 107-93-7 (E)-but-2-enoic acid 
• 73587-63-0 Acetic acid (Z)-3-chloro-1-methyl-3-phenyl-allyl ester 
• 590-14-7 1-bromo-1-propene 
• 106-95-6 allyl bromide 

Downstream Products

• 73172-59-5 [(2RS,3SR)-3-methyloxiran-2-yl]phenylmethanone 
• 57205-23-9 3-Methyl-1-phenyl-2-phenylseleno-1-butanon 
• 22965-93-1 (Z)-2-Bromo-1-phenyl-2-butyn-1-one 
• 53810-72-3 ((1S,2S,3R,4R)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-phenyl-methanone 
• 80674-48-2 3-Hydroxy-3-phenyl-(E)-4-hexensaeure 
• 124306-45-2 (E)-1-Phenyl-4-phenylsulfanyl-but-2-en-1-one 
• 124306-11-2 (Z)-trimethyl((1-phenylbuta-1,3-dien-1-yl)oxy)silane 
• 115534-59-3 erythro-(3-chloro-1-oxo-1-phenyl-2-butyl)phenylselenium dDichloride 
• 97060-53-2 (E,2'RS,3'RS)- and (E,2'RS,3'SR)-1-(3'-hydroxy-2'-methyl-1'-oxo-3'-phenyl-4'-hexenyl)pyrrolidine 
• 164595-89-5 (2'RS,3'RS)- and (2'RS,3'SR)-1-(2',3'-dimethyl-1',5'-dioxo-5'-phenylpentyl)pyrrolidine 
• 122968-58-5 (2'RS,3'RS)-1-(2',3'-dimethyl-1',5'-dioxo-5'-phenylpentyl)pyrrolidine 
• 122969-97-5 (2'RS,3'SR)-1-(2',3'-dimethyl-1',5'-dioxo-5'-phenylpentyl)pyrrolidine 
• 1226-91-1 3-methyl-1,5-diphenyl-pentane-1,5-dione 
• 100662-18-8 (Z)-3-Methyl-1,5-diphenyl-5-trimethylsilanyloxy-pent-4-en-1-one 

Relevant academic research and scientific papers

An efficient synthesis of 2,3,5-trisubstituted furans from α,β- unsaturated ketones

A simple, regioselective synthesis of 2,3,5-trisubstituted furans is described. Conjugate addition of alkynylboronates to α,β-unsaturated ketones, followed by acid-catalyzed cyclization of the resulting γ-alkynyl ketones affords trisubstituted furans in 3197% overall yields.

Activation of Michael Acceptors by Halogen-Bond Donors

Extending earlier studies on iodine catalysis, experimental investigations show that various halogen-bond donors can also be employed to accelerate the Michael addition between trans -crotonophenone and indole. Solvent as well as counteranion effects have been analyzed, and kinetic and computational investigations provide additional insights into the mode of activation.

Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process

Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developedviathe reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated.

N-Heterocyclic Iod(az)olium Salts – Potent Halogen-Bond Donors in Organocatalysis

This article describes the application of N-heterocyclic iod(az)olium salts (NHISs) as highly reactive organocatalysts. A variety of mono- and dicationic NHISs are described and utilized as potent XB-donors in halogen-bond catalysis. They were benchmarked in seven diverse test reactions in which the activation of carbon- and metal-chloride bonds as well as carbonyl and nitro groups was achieved. N-methylated dicationic NHISs rendered the highest reactivity in all investigated catalytic applications with reactivities even higher than all previously described monodentate XB-donors based on iodine(I) and (III) and the strong Lewis acid BF3.

Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures

We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.

Photocatalytic Stoichiometric Oxidant-Free Synthesis of Linear Unsaturated Ketones from 1,2-Disubstituted Cyclopropanols

A one-step catalytic oxidant-free synthesis of unsaturated ketones from 1,2-disubstituted cyclopropanols is reported. Previously for this transformation, only two- and three-step protocols have been developed. The reaction proceeds under irradiation with visible light in the presence of catalytic amounts of both an acridinium photocatalyst and a cobaloxime complex. 2-Aryl-substituted cyclopropanols react giving α,β-unsaturated ketones, while dehydrogenative ring opening of 2-alkyl-substituted substrates affords mixtures of α,β- and β,γ-enones. The reaction starts with one-electron oxidation of a cyclopropanol to cyclopropyloxy radical, presumably, by the photoexcited acridinium catalyst. We also found that Co(dmgBF 2) 2(MeCN) 2complex under an air atmosphere and irradiation with blue LEDs or upon heating can serve as a hydroxycyclopropane oxidant.

Photoredox/Cobalt Dual-Catalyzed Decarboxylative Elimination of Carboxylic Acids: Development and Mechanistic Insight

Recently, dual-catalytic strategies towards the decarboxylative elimination of carboxylic acids have gained attention. Our lab previously reported a photoredox/cobaloxime dual catalytic method that allows the synthesis of enamides and enecarbamates directly from N-acyl amino acids and avoids the use of any stoichiometric reagents. Further development, detailed herein, has improved upon this transformation's utility and further experimentation has provided new insights into the reaction mechanism. These new developments and insights are anticipated to aid in the expansion of photoredox/cobalt dual-catalytic systems.

Enantioselective N -Alkylation of Nitroindoles under Phase-Transfer Catalysis

An asymmetric phase-transfer-catalyzed N -alkylation of substituted indoles with various Michael acceptors was studied. Acidities of nitroindoles were determined in acetonitrile by UV-Vis spectrophotometric titration. There was essentially no correlation between acidity and reactivity in the aza-Michael reaction. The position of the nitro group on the indole ring was essential to control the stereoselectivity of the reaction. Michael adducts were obtained in high yields and moderate enantioselectivities in the reaction between 4-nitroindole and various Michael acceptors in the presence of cinchona alkaloid based phase-transfer catalysts. In addition to outlining the scope and limitations of the method, the geometries of the transition states of the reaction were calculated.

Electrochemical C(sp 3)-H Fluorination

A simple and robust method for electrochemical alkyl C-H fluorination is presented. Using a simple nitrate additive, a widely available fluorine source (Selectfluor), and carbon-based electrodes, a wide variety of activated and unactivated C-H bonds are converted into their C-F congeners. The scalability of the reaction is also demonstrated with a 100 gram preparation of fluorovaline.

Organocatalytic Enantioselective Selenosulfonylation of a C-C Double Bond to Form Two Stereogenic Centers in an Aqueous Medium

Organocatalytic selenosulfonylation of the C-C double bond of α,β-unsaturated ketones to construct two contiguous stereogenic centers in an aqueous medium was described. A series of α-selenyl and β-sulfonyl ketones with various functional groups were synthesized in good yields and enantioselectivities with saturated NaCl solution as the solvent. In addition, this protocol had been successfully scaled up to a decagram scale via a simple workup procedure.