40240-72-0

Upstream product

• 110533-48-7 (4-methoxy-phenacyl)-dimethyl-phenacyl-ammonium; bromide 
• 31378-03-7 1-phenyl-2-tosylethanone 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 140156-00-9 1-methyl-4-(2-phenylallyl)benzene 
• 530-48-3 1,1-Diphenylethylene 
• 5700-44-7 1-phenyl-1-cyclohexylethylene 
• 19523-28-5 1-methyl-4-(2-phenyl-2-prop-2-ene-1-sulfonyl)-benzene 
• 128318-85-4 1-(1-azidoprop-2-en-2-yl)benzene 
• 16307-59-8 N-(2-phenyl-2-propenyl)phthalimide 
• 1374016-46-2 N-(2-phenylallyl)-N-(phenylsulfonyl)benzenesulfonamide 
• 56865-72-6 2-Phenyl-3-(phenylamino)-1-propene 
• 86148-32-5 2-phenyl-2-propen-1-ol benzoate 
• 1231245-70-7 C₁₅H₁₃Cl 
• 93273-60-0 1-methoxy-3-(2-phenylallyl)benzene 

Downstream Products

• 144774-54-9 (Z)-1-(4-methoxyphenyl)-4-phenylbut-2-ene-1,4-dione 
• 60755-22-8 1-(4-methoxyphenyl)-4-phenyl-1,4-butanedione 

Relevant academic research and scientific papers

Copper-Catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon-Carbon Bonds of 1,1-Disubstituted Alkenes with Sulfonyl Hydrazides

Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations. However, carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen, is scarce and underdeveloped. Herein, we report alkoxy radical, which was generated from alkyl radical and dioxygen, mediated selective cleavage of unstrained carbon-carbon bond for the oxysulfonylation of 1,1-disubstituted alkenes, providing facile access to a variety of valuable β-keto sulfones. Mechanistic experiments indicated alkoxy radical intermediate that underwent subsequent regioselective β-scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C—C bond cleavage. Notably, the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.

Aerobic Oxidative Dehydrogenation of Ketones to 1,4-Enediones

An efficient and unprecedented strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation. The protocol employs molecular oxygen as the sole oxidant and represents an atom- and step-economic process. The approach showed broad substrate scope, good functional group tolerance, and complete E-stereoselectivity. The reaction mechanism has been investigated through deuterium-labeling experiments and intermediate experiments.

Visible-Light-Driven Stereoselective Annulation of Alkyl Anilines and Dibenzoylethylenes via Electron Donor-Acceptor Complexes

A catalyst-free, stereoselective visible-light-driven annulation reaction between alkenes and N,N-substituted dialkyl anilines for the synthesis of substituted tetrahydroquinolines is presented. The reaction is driven by the photoexcitation of an electron donor-acceptor (EDA) complex, and the resulting products are obtained in good to high yields with complete diastereoselectivity. Mechanistic rationale and photochemical characterization of the EDA-complex are provided.

Proton-Coupled Electron Transfer: Transition-Metal-Free Selective Reduction of Chalcones and Alkynes Using Xanthate/Formic Acid

Highly chemoselective reduction of α,β-unsaturated ketones to saturated ketones and stereoselective reduction of alkynes to (E)-alkenes has been developed under a transition-metal-free condition using a xanthate/formic acid mixture through proton-coupled electron transfer (PCET). Mechanistic experiments and DFT calculations support the possibility of a concerted proton electron-transfer (CPET) pathway. This Birch-type reduction demonstrates that a small nucleophilic organic molecule can be used as a single electron-transfer (SET) reducing agent with a proper proton source.

Synthesis of (E)-1,4-diaryl-2-butene-1,4-diones

We report a facile route for the preparation of symmetric and unsymmetric (E)-1,4-diaryl-2-butene-1,4-diones 3 by a two-step route, including (1) nucleophilic substitution of 1 with sulfinic acid sodium salts, and (2) K2CO3 mediated alkylation of β-ketosulfones 4 with 1 followed by sequential desulfonylation of the resulting 1,4-diketones 5 in acetone. These products were obtained in high yields.

Visible-light-mediated oxidative dimerization of arylalkynes in the open air: Stereoselective synthesis of (Z)-1,4-enediones

An organic photoredox catalytic one-pot protocol is developed for the highly stereoselective synthesis of (Z)-1,4-enediones. The reaction starts directly from alkyne precursors, using 4-(4-cyanophenyl)-2,6-diphenylpyrylium tetrafluoroborate (CN-TPT) as an efficient photosensitizer and dioxygen in the air as a green oxidant. A Csp-Csp oxidative coupling/[4 + 2] cyclization (with dioxygen)/fragmentive isomerization cascade mechanism was proposed. The predominant formation of (Z)-1,4-enediones is attributed to the efficient visible-light illumination from blue LEDs, along with possible energy transfer from the photosensitizer CN-TPT to the E-isomers.

Synthesis of (E)-1,4-enediones from α-halo ketones through a sodium sulfinate mediated reaction

We developed a mild and practical protocol for the synthesis of 1,4-enedione from α-halo ketones through a sodium sulfinate mediated reaction. This reaction enables the construction of symmetric and unsymmetric 1,4-enedione with complete E selectivity. Sodium 4-toluenesulfinate plays an important role in this reaction.

A highly tunable stereoselective dimerization of methyl ketone: Efficient synthesis of e - And Z-1,4-enediones

A new method for the tunable synthesis of 1,4-enedione directly from aromatic methyl ketone is described. This tandem reaction enables the construction of symmetric and unsymmetric 1,4-enediones with complete E-selectivity. Moreover, the resulting E-1,4-enedione could be transformed into a Z-isomer by irradiation with 23 W of white light.