688799-40-8

Upstream product

• 14267-92-6 1-chloro-4-pentyne 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 77758-50-0 4-pentynyl-1-tosylate 
• 35761-91-2 5-iodo-1-trimethylsilyl-1-pentyne 
• 2468-55-5 5-iodopent-1-yne 
• 98-86-2 acetophenone 

Downstream Products

• 1170145-36-4 C₁₆H₁₇⁽²⁾HO₃ 
• 15288-74-1 1-phenyl-6-heptyn-1-one 

Relevant academic research and scientific papers

Aromaticity-Driven Access to Cycloalkyl-Fused Naphthalenes

We report the efficient synthesis of cycloalkyl-fused naphthalenes through the [4 + 2]-cycloaddtion/decarboxylative aromatization of alkyne-tethered aryne insertion adducts. These scaffolds were difficult to synthesize using conventional reactions. The reaction proceeds via the formation of a benzopyrylium intermediate followed by intramolecular [4 + 2] cycloaddition and a subsequent decarboxylation pathway. This method is also compatible with allene-tethered substrates to afford similar products. In addition, the one-pot synthesis of polysubstituted naphthalenes via aryne insertion/benzannulation has also been developed in good yield.

Stereoselective Radical Cyclization Cascades Triggered by Addition of Diverse Radicals to Alkynes to Construct 6(5)-6-5 Fused Rings

Cascade radical cyclization of alkynyl ketones with various carbon- and heteroatom-centered radical precursors via a sequential radical addition/1,5-H radical shift/5-exo-trig/radical cyclization process was realized for the first time. This method provides a strategically novel and step-economical protocol for diversity-oriented synthesis of a wide range of carbocyclic and heterocyclic 6(5)-6-5 fused ring systems with three contiguous stereocenters, including a quaternary carbon in high yields with excellent chemo- and diastereoselectivity.

Palladium(0)/copper(I)-catalyzed tandem cyclization of aryl 1-cyanoalk-5-ynyl ketone system: Rapid assembly of cyclopenta[b]naphthalene and benzo[b]fluorene derivatives

We have developed a new and general approach to construct a variety of benzo[b]fluorene and cyclopenta-[b]naphthalene derivatives via the palladium(0)/copper(I)-catalyzed tandem cyclization of aryl 1-cyanoalk-5-ynyl ketone systems in an extremely efficient manner. The key operation lies in the copper(I)-catalyzed aerobic oxidation, which allows for activation of two successive intramolecular cycloadditions immediately after the Sonogashira coupling reaction has occurred. Copyright

La/Ag heterobimetallic cooperative catalysis: A catalytic asymmetric conia-ene reaction

A dual catalyst system: The cooperative function of a hard and soft Lewis acid (LaIII and AgI, respectively) in a catalyst system that includes an amide-based ligand 1 is crucial for simultaneous activation of intramolecular 1,3-dicarbonyl and alkyne moieties to afford enantioenriched cyclopentane derivatives (see scheme). Copyright

Boronic acid catalyzed ene carbocyclization of acetylenic dicarbonyl compounds

The discovery and development of an efficient ene carbocyclization of 1,3-dicarbonyl compounds bearing pendent terminal alkyne substituents under 3-nitrobenzeneboronic acid catalysis is described. The reaction is efficient, easy to perform and general to a wide range of ketoester substrates.

General zinc-catalyzed Conia-ene reactions of 1,3-dicarbonyl compounds with alkynes including the classically challenging substrates under neat conditions

A simple, versatile new approach to fourmembered ring to six-membered ring products has been developed by zinc-catalyzed intramolecular Conia-ene reactions of 1,3-dicarbonyl compounds with alkynes. This new route allows a wide range of dicarbonyl compounds, including the classically challenging 1,3-diesters and N,N'-disubstituted 1,3-keto amides, to be used for the Conia-ene reaction with inexpensive zinc chloride (ZnCl2) under neat conditions.

Bronsted base/Lewis acid cooperative catalysis in the enantioselective Conia-ene reaction

(Chemical Equation Presented) A mutually compatible and cooperative combination of copper(I) triflate and bifunctional 9-amino-9-deoxyepicinchona- derived urea compounds for the enantioselective Conia-ene cyclization of alkyne-tethered β-ketoester substrates is reported. The reaction is efficient, broad in scope, and easy to perform and allows access to chiral methylenecyclopentane products with high enantiocontrol. The transformation illustrates the concept of combining inactive precatalysts with inactive transition-metal-ion complexes in situ to reversibly create a catalytically active combination of the two.