72946-35-1

Upstream product

• 1006720-42-8 3-cyclohexylidene-1-phenylprop-2-en-1-one 
• 853994-91-9 1-(2-phenylethynyl)-8-oxabicyclo[5.1.0]octane 
• 100-42-5 styrene 
• 502-42-1 cycloheptanone 
• 145343-92-6 C₇H₁₁IO 
• 536-74-3 phenylacetylene 
• 1121-66-0 2-Cyclohepten-1-one 
• 160878-96-6 α-iodocycloheptenone 

Relevant academic research and scientific papers

A convenient synthesis of highly substituted furans by microwave irradiation of ring-fused alkylidenecyclopropanes

Microwave irradiation of ring-fused alkylidenecyclopropanes under solvent-free conditions afforded highly substituted furans in good yields.

Copper/P(tBu)3-Mediated Regiospecific Synthesis of Fused Furans and Naphthofurans

A novel [3+2] cycloaddition between a variety of cyclic ketones and diverse olefins or alkynes can be effectively promoted by copper in combination with the tri-tert-butylphosphine [P(tBu)3] ligand. This protocol exhibits excellent selectivity and provides an exemplary set of fused heterocycles in good to excellent yields. Present strategy also represents an extremely simple and atom-economic way to construct substituted fused furans and naphthofurans from readily available starting materials under mild reaction conditions. The utility of the method is further demonstrated by the synthesis of chiral furans from (R)-(?)-carvone and (S)-(+)-carvone. A plausible mechanism involving the oxidative radical cyclization has been suggested based on experimental observations.

Extrapolation of the gold-catalyzed cycloisomerization to the palladium-catalyzed cross-coupling/cycloisomerization of acetylenic alcohols for the synthesis of polysubstituted furans: Scope and application to tandem processes

This paper describes the development of an integrated approach for the preparation of diverse furan derivatives from acetylenic alcohols by gold and palladium catalyzed π-activation chemistry. Notably, this new method was found to be amenable to cycloocty

Syntheses of substituted furans and pyrroles by platinum-catalyzed cyclizations of propargylic oxiranes and aziridines in aqueous media

The reactions of propargylic oxiranes and aziridines with a platinum catalyst in aqueous media are described. Furans having a variety of substituents were conveniently synthesized by the platinum-catalyzed reaction of propargylic oxiranes. The reaction in the presence of N-iodosuccinimide afforded the 3-iodo-substituted furan, which was further functionalized to tetrasubstituted furans with high efficiency. Propargylic aziridines were also reacted with the platinum catalyst to produce the corresponding substituted pyrroles in good yields. Georg Thieme Verlag Stuttgart.

Synthesis of substituted furans by platinum-catalyzed cyclization of propargylic oxiranes in aqueous media

The reaction of propargylic oxiranes with platinum catalyst in aqueous media is described. Furans having a variety of substituents were conveniently synthesized with high efficiency.

Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles

A general, mild, and efficient 1,2-migration/cycloisomerization methodology toward multisubstituted 3-thio-, seleno-, halo-, aryl-, and alkyl-furans and pyrroles, as well as fused heterocycles, valuable building blocks for synthetic chemistry, has been developed. Moreover, regiodivergent conditions have been identified for C-4 bromo- and thio-substituted allenones and alkynones for the assembly of regioisomeric 2-hetero substituted furans selectively. It was demonstrated that, depending on reaction conditions, ambident substrates can be selectively transformed into furan products, as well as undergo selective 6-exo-dig or Nazarov cyclizations. Our mechanistic investigations have revealed that the transformation proceeds via allenylcarbonyl or allenylimine intermediates followed by 1,2-group migration to the allenyl sp carbon during cycloisomerization. It was found that 1,2-migration of chalcogens and halogens predominantly proceeds via formation of irenium intermediates. Analogous intermediate can also be proposed for 1,2-aryl shift. Furthermore, it was shown that the cycloisomerization cascade can be catalyzed by Bransted acids, albeit less efficiently, and commonly observed reactivity of Lewis acid catalysts cannot be attributed to the eventual formation of proton. Undoubtedly, thermally induced or Lewis acid-catalyzed transformations proceed via intramolecular Michael addition or activation of the enone moiety pathways, whereas certain carbophilic metals trigger carbenoid/oxonium type pathway. However, a facile cycloisomerization in the presence of cationic complexes, as well as observed migratory aptitude in the cycloisomerization of unsymmetrically disubstituted aryl- and alkylallenes, strongly supports electrophilic nature for this transformation. Full mechanistic details, as well as the scope of this transformation, are discussed.