712278-61-0

Upstream product

• 3378-82-3 1-bromo-2-naphthaldehyde 
• 536-74-3 phenylacetylene 

Downstream Products

• 712278-63-2 1-[1-(phenylethynyl)naphthalen-2-yl]-3-(trimethylsilyl)-2-propyn-1-ol 
• 895532-23-7 2-ethynyl-1-(phenylethynyl)naphthalene 
• 1382352-91-1 2-phenyl-4H-benzo[f ]isochromen-4-one 

Relevant academic research and scientific papers

Tunable Synthesis of Indeno[1,2- c]furans and 3-Benzoylindenones via FeCl3-Catalyzed Carbene/Alkyne Metathesis Reaction of o-Alkynylbenzoyl Diazoacetates

An efficient synthesis of indeno[1,2-c]furan and 3-benzoylindenone derivatives through a FeCl3-catalyzed carbene/alkyne metathesis reaction of o-alkynylbenzoyl diazoacetates is presented. Mechanistically, the key intermediate, vinyl iron carbene, is formed by 5-exo-dig carbocyclization and terminated with a formal [3 + 2] cycloaddition or carbonylation. To the best of our knowledge, this is the first example in which FeCl3 is used as a catalyst for a carbene/alkyne metathesis reaction. Finally, derivatization reactions were carried out to showcase the value of the products.

Modular synthesis of 3-substituted isocoumarinsviasilver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes

A method involving silver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes to yield 3-substituted isocoumarins is described. The developed protocol allows convenient access to a range of synthetically useful 3-substituted isocoumarins and related fused heterocyclolactones in good to high yields, using silver tetrafluoroborate as the catalyst, and atmospheric oxygen as the terminal oxidant and the source of endocyclic oxygen. Mechanistic studies suggest the involvement of a free-radical pathway.

Radical Cascade Bicyclization/Aromatization of 1,7-Enynes with 1,3-Dicarbonyl Compounds towards 2,3-Dihydro-1H-cyclopenta[a]naphthalenes

An Ag-catalyzed radical cascade bicyclization/aromatization of C-linked 1,7-enynes with 1,3-dicarbonyls has been achieved, providing a step- and atom-economy approach for the construction of 2,3-dihydro-1H-cyclopenta[a]naphthalenes, an important structural scaffold existed in biologically active compounds. From this transformation, structurally diverse 2,3-dihydro-1H-cyclopenta[a]naphthalenes were obtained in moderate to good yields with high regioselectivity. Moreover, the further product derivatizations were also exemplified. (Figure presented.).

Palladium-catalyzed cascade decarboxylative amination/6- endo-dig benzannulation of o-alkynylarylketones with n-hydroxyamides to access diverse 1-naphthylamine derivatives

An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.

Carbonyl-Directed Addition of N-Alkylhydroxylamines to Unactivated Alkynes: Regio- and Stereoselective Synthesis of Ketonitrones

A variety of ketonitrones were synthesized in moderate to excellent yields with high chemo-, regio-, and stereoselectivity by using carbonyl-directed addition of N-alkylhydroxylamines to unactivated alkynes under mild conditions. The product diverisity could be controlled by the use of different bases, and EtN(n-Pr)2 could promote the formation of ketonitrones while using EtONa as base led to indanone-derived nitrones. Control experiments indicated that the carbonyl group of the substrate acted as an H-bond acceptor except for an electron-withdrawing group, and conjugated enone skeleton accounted for the high selectivity.

Synthesis of Functionalized Cyclobutane-Fused Naphthalene Derivatives via Cascade Reactions of Allenynes with tert-Butyl Nitrite

A novel synthesis of cyclobutanol-fused 2-nitronaphthalen-1-ols and nitrocyclobutane-fused naphthalene-1,2-diones through cascade reactions of benzene-linked allenynes with tert-butyl nitrite is presented. The formation of the title compounds involves a tandem process including allenyne [2+2] cycloaddition, radical addition onto the in situ formed cyclobutenyl moiety followed by radical coupling/oxidation. Interestingly, different kinds of functionalized naphthalene derivatives could be obtained selectively from the same substrates, and the selectivity was easily controlled by finely tuning the reaction conditions. (Figure presented.).

Highly Chemo-, Regio- and E/Z-Selective Intermolecular Heck-Type Dearomative [2 + 2 + 1] Spiroannulation of Alkyl Bromoarenes with Internal Alkynes

Described herein is a palladium-catalyzed dearomative annulation of alkyl bromoarenes with internal alkynes. Challenges in this spiroannulation include the chemoselectivity among [2 + 2 + 1], [2 + 2 + 2], and [3 + 2] annulations and the E/Z-selectivity associated with the generated exocyclic double bond. In the presence of Pd(OAc)2 and a phosphine ligand, a variety of highly functionalized spirocyclopentadienes with an exocyclic carbon-carbon double bond are provided in good to excellent yields with high chemo-, regio-, and E/Z-selectivity via a Heck-type pathway.

A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes

A unique gold(i)-catalyzed 5-endo-dig cyclization/aerobic oxidation cascade strategy from 1,5-enyne substrates with molecular oxygen as the oxidant to yield the indenone was described. The reaction mechanism was studied by heavy atom labelling and some related experiments. This method was applied to the formal total synthesis of isoprekinamycin.

A gold(i)-catalyzed intramolecular tandem cyclization reaction of alkylidenecyclopropane-containing alkynes

A novel gold(i)-catalyzed intramolecular tandem cyclization reaction of ortho-(arylethynyl)arenemethylenecyclopropanes provided an efficient approach to prepare functionalized 11H-benzo[a]fluorene derivatives in moderate to good yields. Further transformations as well as applications of the products have been presented and a plausible reaction mechanism has also been proposed on the basis of deuterium labeling and control experiments.

Highly selective construction of medium-sized lactams by palladium-catalyzed intramolecular hydroaminocarbonylation of aminoalkynes

A novel palladium-catalyzed intramolecular hydroaminocarbonylation of aminoalkynes has been developed. This direct and operationally simple protocol provides a rapid and reliable approach to a diverse array of valuable seven-and eight-membered lactams with high chemoselectivity and regioselectivity. The high selectivity might be attributed to rational tuning the electronic nature of the amine moiety and the palladium catalyst which enabled this transformation to proceed in the absence of acidic or any other additives under fairly mild reaction conditions. This method paves the way for the synthesis of medium-sized lactams.