35030-91-2

Upstream product

• 65-85-0 benzoic acid 
• 931-49-7 1-ethenylcyclohexene 
• 931-48-6 2-cyclohexylacetylene 
• 98-88-4 benzoyl chloride 
• 1415426-00-4 (E)-3-chloro-3-cyclohexyl-1-phenylprop-2-en-1-one 
• 1192-88-7 1-cyclohexene-1-carboxaldehyde 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 

Relevant academic research and scientific papers

Direct Access to α,β-Unsaturated Ketones via Rh/MgCl2-Mediated Acylation of Vinylsilanes

We report herein the facile and practical construction of α,β-unsaturated ketones via rhodium-catalyzed direct acylation of vinylsilanes with readily available and abundant carboxylic acids. This protocol features access to a diverse array of synthetically useful functionalities with moderate to excellent yields. More importantly, the late-stage functionalization of pharmaceuticals was also realized with synthetically useful yield.

Tandem Transformations via Friedel-Crafts Acylation Followed by a Ring-Expansion, Ring-Opening, and Cycloisomerization Sequence

A tandem synthetic route to a diverse array of cyclic compounds has been developed from Friedel-Crafts acylation of alkynes followed by the microwave irradiation of β-chlorovinyl ketone intermediates. The stereoisomeric β-chlorovinyl ketone intermediates smoothly underwent a thermal α-vinyl enolization and ring expansion to vinyl and carbocyclic furans as well as cyclopetene derivatives in good to excellent yields without the need for any catalysts.

1,3-Dienones and 2H-Pyran-2-ones from Soft α-Vinyl Enolization of β-Chlorovinyl Ketones: Defined Roles of Br?nsted and Lewis Base

The eliminative reaction pathways of (E)-β-chlorovinyl ketones were investigated in the presence of both Br?nsted and Lewis bases. The Br?nsted base, Et3N, effected the soft α-vinyl enolization of (E)-β-chlorovinyl ketones to [3]cumulenol intermediates; in turn, a catalytic amount of Lewis base, PPh3, initiated isomerization to provide 1,3-dienones in high yields. The introduction of a carbon-based nucleophile into the reaction mixture provided the highly efficient synthetic route to 2H-pyran-2-ones in one pot, where the carbon-based nucleophile generated by an extra equivalent of Br?nsted base, Et3N, attacked the electrophilic [3]cumulenol intermediates to initiate cyclization to give 2H-pyran-2-ones.

Amine-promoted synthesis of vinyl aziridines

N-Unsubstituted vinyl aziridines were synthesized via an amine-promoted regioselective nucleophilic aziridination of α,β,γ,δ- unsaturated carbonyl compounds. The reaction is completely regioselective (>95: 5) for the α,β-alkene and completely diastereosel