202932-64-7

Upstream product

• 2622-05-1 allylmagnesium bromide 
• 17077-46-2 4-(3-phenyl-propionyl)-morpholine 
• 645-45-4 hydrocinnamic acid chloride 
• 1730-25-2 allylmagnesium bromide 
• 60340-28-5 1-phenylhex-5-en-3-ol 
• 104-53-0 3-phenyl-propionaldehyde 
• 73086-81-4 1-allyl-2,4,6-triphenylpyridin-1-ium tetrafluoroborate salt 
• 458-69-5 3-phenylpropanoic acid fluoride 
• 762-72-1 allyl-trimethyl-silane 
• 501-52-0 3-Phenylpropionic acid 
• 170646-96-5 N-methoxy-N-methyl-3-phenylpropionamide 
• 106-95-6 allyl bromide 

Downstream Products

• 1588-44-9 6-phenyl-1-hexene 
• 60550-53-0 1-phenyl-4-hexen-3-one 
• 1158843-57-2 C₁₂H₁₄O₂ 
• 116628-22-9 1,6-diphenylhexan-3-one 

Relevant academic research and scientific papers

Indium-catalyzed reduction of allyl bromide with gallium or aluminum. Formation of allylgallium and allylaluminum sesquibromides

Matrix presented Fast transmetalation of an allyl group from indium to gallium enables the assembly of a catalytic cycle of indium, which accelerates the formation of allylgallium sesquibromide. A solution of allylaluminum sesquibromide in THF is also pre

A convenient synthesis of β,γ-unsaturated ketones through zinc-mediated allylation of acid chlorides

An efficient procedure for the preparation of β,γ-unsaturated ketones has been developed by a simple reaction of an acid chloride with allyl bromide and commercial zinc dust in ether.

Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton

An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ-hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo- and 86% to >99% enantioselectivities from a range of substituted isatins and γ-hydroxy enones. (Figure presented.).

Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes

A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.

Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines

A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.

C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis

Catalyst controlled site-selective C-H functionalization is a challenging but powerful tool in organic synthesis. Polarity-matched and sterically controlled hydrogen atom transfer (HAT) provides an excellent opportunity for site-selective functionalization. As such, the dual Ni/photoredox system was successfully employed to generate acyl radicals from aldehydes via selective formyl C-H activation and subsequently cross-coupled to generate ketones, a ubiquitous structural motif present in the vast majority of natural and bioactive molecules. However, only a handful of examples that are constrained to the use of aryl halides are developed. Given the wide availability of amines, we developed a cross-coupling reaction via C-N bond cleavage using the economic nickel and TBADT catalyst for the first time. A range of alkyl and aryl aldehydes were cross-coupled with benzylic and allylic pyridinium salts to afford ketones with a broad spectrum of functional group tolerance. High regioselectivity toward formyl C-H bonds even in the presence of α-methylene carbonyl or α-amino/oxy methylene was obtained.

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.

N-Hydroxybenzimidazole as a structurally modifiable platform forN-oxyl radicals for direct C-H functionalization reactions

Methods for direct functionalization of C-H bonds mediated byN-oxyl radicals constitute a powerful tool in modern organic synthesis. While severalN-oxyl radicals have been developed to date, the lack of structural diversity for these species has hampered further progress in this field. Here we designed a novel class ofN-oxyl radicals based onN-hydroxybenzimidazole, and applied them to the direct C-H functionalization reactions. The flexibly modifiable features of these structures enabled facile tuning of their catalytic performance. Moreover, with these organoradicals, we have developed a metal-free approach for the synthesis of acyl fluoridesviadirect C-H fluorination of aldehydes under mild conditions.

Lewis Acid Catalyzed [3+3] Annulation of Donor–Acceptor Cyclopropanes with γ-Hydroxyenones: Access to Highly Functionalized Tetrahydropyrans

Donor–acceptor cyclopropanes were engaged in a [3+3]-annulation reaction with γ-hydroxyenones. Sc(OTf)3was found to be the best catalyst, and 2,4,4,5-tetrasubstituted tetrahydropyran products were obtained in good yields under mild reaction con

Controlling the α/γ-Reactivity of Vinylogous Ketone Enolates in Organocatalytic Enantioselective Michael Reactions

The first regio-, diastereo-, and enantioselective direct Michael reaction of β,γ-unsaturated ketones with nitroolefins is enabled by Br?nsted base/hydrogen-bonding bifunctional catalysis. A squaramide-substituted tertiary amine catalyzes the reaction of a broad range of β,γ-unsaturated ketones to proceed at the α-site exclusively, giving rise to adducts with two consecutive tertiary carbon stereocenters in diastereomeric ratios of up to >20:1 and enantioselectivities generally in the 90–98 % ee range.