84624-35-1

Upstream product

• 34434-35-0 Natrium-Verbindung des Cyclohexanons 
• 4392-24-9 Cinnamyl bromide 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 21040-45-9 Cinnamyl acetate 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 117969-61-6 [(1E)-3-fluoroprop-1-en-1-yl]benzene 
• 108-94-1 cyclohexanone 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 17851-97-7 1-tri(n-butyl)stannyloxy-1-cyclohexene 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 108-86-1 bromobenzene 
• 673-32-5 1-Phenylprop-1-yne 

Downstream Products

• 153124-74-4 2-(2,2-Dimethoxy-acetyl)-6-((E)-3-phenyl-allyl)-cyclohexanone 
• 153124-75-5 2-(4-Fluoro-phenyl)-7-((E)-3-phenyl-allyl)-4,5,6,7-tetrahydro-2H-indazole-3-carbaldehyde 

Relevant academic research and scientific papers

Direct Enantioselective α-Allylation of Unfunctionalized Cyclic Ketones with Alkynes through Pd-Amine Cooperative Catalysis

The first direct enantioselective α-allylation of unfunctionalized cyclic ketones using alkynes as an economical choice of reagent is reported. This transformation uses a simple procedure with commercially available palladium, chiral bisphosphine ligand and chiral amine catalysts, and affords valuable ketones with a α-tertiary stereocenter in good to high enantiopurity. In this transformation, a chiral palladium complex containing the (S)-DIFLUORPHOS ligand catalyzes the isomerization of alkynes into an electrophilic allylpalladium species, which is attacked by the enamine generated in situ from the condensation of (R)-prolinol with the ketone substrate.

Cooperative Palladium/Proline-Catalyzed Direct α-Allylic Alkylation of Ketones with Alkynes

The cooperative palladium/l-proline-catalyzed direct α-allylic alkylation of ketones with alkynes is achieved. This reaction exhibits high atom economy since a leaving group is not liberated and a stoichiometric amount of extra oxidant is not needed. A br

Palladium-catalyzed allylic alkylation of simple ketones with allylic alcohols and its mechanistic study

Allylic alcohols were directly used in Pd-catalyzed allylic alkylations of simple ketones under mild reaction conditions. The reaction proceeded smoothly at 20°C by the concerted action of a Pd catalyst, a pyrrolidine co-catalyst, and a hydrogen-bonding solvent, and does not require any additional reagents. A computational study suggested that methanol plays a crucial role in the formation of the π-allylpalladium complex by lowering the activation barrier. Concerted action: Allylic alcohols were directly used in the title reaction under mild conditions. The reaction smoothly proceeds by the concerted action of a Pd catalyst, a pyrrolidine co-catalyst, and a hydrogen-bonding solvent, and does not require any additional reagents. A computational study suggested that methanol plays a crucial role in the formation of the π-allylpalladium complex by lowering the activation barrier.

Hydrogen-bond-activated palladium-catalyzed allylic alkylation via allylic alkyl ethers: Challenging leaving groups

C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).

Catalytic olefin hydroamination with aminium radical cations: A photoredox method for direct C-N bond formation

While olefin amination with aminium radical cations is a classical method for C-N bond formation, catalytic variants that utilize simple 2° amine precursors remain largely undeveloped. Herein we report a new visible-light photoredox protocol for the intramolecular anti-Markovnikov hydroamination of aryl olefins that proceeds through catalytically generated aminium radical intermediates. Mechanistic studies are consistent with a process involving amine oxidation via electron transfer, turnover-limiting C-N bond formation, and a second electron transfer step to reduce a carbon-centered radical, rendering the overall process redox-neutral. A range of structurally diverse N-aryl heterocycles can be prepared in good to excellent yields under conditions significantly milder than those required by conventional aminium-based protocols.

Direct catalytic intermolecular α-allylic alkylation of aldehydes by combination of transition-metal and organocatalysis

(Chemical Equation Presented) All in the same pot together: The direct catalytic α-allylic alkylation of aldehydes and cyclic ketones is achieved by using a simple, unprecedented one-pot procedure. Transition-metal and enamine catalysis are combined so that α-allylic alkylated aldehydes and cyclic ketones are formed in high yield with a direct catalytic chemo- and regioselective method.

Boron trifluoride-catalyzed reaction of alkyl fluoride with silyl enolate, allylsilane, and hydrosilane

Alkylation of silyl enolates with tert-alkyl or allylic fluorides proceeds smoothly in the presence of a catalytic amount of boron trifluoride to afford the corresponding carbonyl compounds. Allylation and reduction of alkyl fluorides with allylsilane and hydrosilane, respectively, occur under BF 3 catalysis.

Tandem cyclization of N-allylaminyl radicals: Stereoselective synthesis of 1,2,5-trisubstituted pyrrolizidines

Radical reaction of N-allylalk-4-enylaminyl radicals, generated from the corresponding N-chloroamines by treatment with Bu3SnH-AIBN in refluxing toluene, was carried out. Tandem cyclization of the resulting neutral aminyl radicals readily took

Kinetics and mechanisms of the reactions of π-allylpalladium complexes with nucleophiles

Which nucleophiles are capable of attacking the allyl ligand of the Pd- stabilized allyl cation 1? This question is answered by the electrophilicity parameter of 1 which is derived from kinetic investigations.