57542-05-9

Upstream product

• 13735-81-4 1-styrenyloxytrimethylsilane 
• 504-61-0 (E)-but-2-enol 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 4784-77-4 (E/Z)-crotyl bromide 
• 98-86-2 acetophenone 
• 34434-33-8 sodium acetophenoxide 
• 126435-82-3 [1-(1-Methyl-allyloxy)-vinyl]-benzene 
• 101089-01-4 (E)-ethyl 2-benzoylhex-4-enoate 
• 542-72-3 (E)-but-2-en-1-ol 
• 532-27-4 1-chloroacetophenone 
• 17851-98-8 1-phenyl-1-(tributylstannyloxy)ethene 
• 591-97-9 1-chloro-2-butene 
• 15482-43-6 1-benzoyl-2-vinylcyclopropane 

Downstream Products

• 4535-44-8 (E)-1-phenylhex-4-ene-1-ol 
• 182144-39-4 C₁₂H₁₅O 
• 139909-12-9 6-Chloro-6-phenyl-2-hexene 
• 59321-58-3 1-Phenyl-4-hexen-1-ol 
• 59361-03-4 (E)-2-phenylhept-5-en-2-ol 

Relevant academic research and scientific papers

Selective Synthesis of Z-Silyl Enol Ethers via Ni-Catalyzed Remote Functionalization of Ketones

We report a remote functionalization strategy, which allows the Z-selective synthesis of silyl enol ethers of (hetero)aromatic and aliphatic ketones via Ni-catalyzed chain walking from a distant olefin site. The positional selectivity is controlled by the directionality of the chain walk and is independent of thermodynamic preferences of the resulting silyl enol ether. Our mechanistic data indicate that a Ni(I) dimer is formed under these conditions, which serves as a catalyst resting state and, upon reaction with an alkyl bromide, is converted to [Ni(II)-H] as an active chain-walking/functionalization catalyst, ultimately generating a stabilized η3-bound Ni(II) enolate as the key selectivity-controlling intermediate.

Radical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing N-Heterocycles via Dual Cobaloxime and Photoredox Catalysis

Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive molecules. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermolecular cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole products in satisfactory yields. In the presence of external alkenes, the tandem reaction generates E-selective coupling products with excellent chemo- and stereoselectivity.

Water-Accelerated Nickel-Catalyzed α-Crotylation of Simple Ketones with 1,3-Butadiene under pH and Redox-Neutral Conditions

We report a nickel/NHC-catalyzed branched-selective α-crotylation of simple ketones using 1,3-butadiene as the alkylation agent. This reaction is regioselective and operated under pH and redox-neutral conditions. Water was used as the sole additive, which significantly accelerates the transformation.

Diverse N-Heterocyclic Ring Systems via Aza-Heck Cyclizations of N-(Pentafluorobenzoyloxy)sulfonamides

Aza-Heck cyclizations initiated by oxidative addition of Pd0-catalysts into the N?O bond of N-(pentafluoro-benzoyloxy)sulfonamides are described. These studies, which encompass only the second class of aza-Heck reaction developed to date, provide direct access to diverse N-heterocyclic ring systems.

Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the SRN1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

Pd-catalyzed domino carbonylative-decarboxylative allylation: An easy and selective monoallylation of ketones

In the presence of an allyl alcohol, α-chloroacetophenones undergo an allyloxycarbonylation reaction followed by in situ decarboxylative allylation to selectively afford the corresponding monoallylated ketones via a Pd-catalyzed domino sequence. The scope of the reaction was extended to substituted α-chloroacetophenones as well as various allyl alcohols.

Cobalt-catalyzed aerobic oxidation of (E)- and (Z)-bishomoallylic alcohols

Stereoselectivity for (5-phenyltetrahydrofur-2-yl)alkan-1-ol formation (cis:trans 1:99) from 5-methyl- and 5-phenyl-substituted 1-phenylpent-4-en-1-ols via cobalt-catalyzed aerobic oxidation was independent of the olefinic π-bond configuration of the su

Regioselective and enantioselective iridium-catalyzed allylation of enamines

A highly enantioselective and regioselective monoallylation of the enamines of methyl ketones has been developed. After hydrolysis of the enamine (NaOAc/AcOH(aq)), the desiredallylated ketones were obtained in high yields (64-91% isolated yield

Ir-catalyzed regio- and enantioselective decarboxylative allylic alkylations

[Ir(COD)Cl]2/phosphoramidite ligand 1a was found to be an efficient catalytic system, for the highly regio- and enantioselective decarboxylative alkylation of γ-substltuted allyl β-ketocarboxylates, affording the branched products with up to >99/1 branched-linear ratio and 96% ee.

Synthesis of polysubstituted tetrahydrofurans via Pd-catalyzed carboetherification reactions

Pd-catalyzed carboetherifications of 1-, 2-, or 3-substituted γ-hydroxy internal alkenes afford tetrahydrofuran products bearing three stereocenters in good yield with moderate to good stereoselectivity.