478282-11-0

Upstream product

• 66-99-9 β-naphthaldehyde 
• 536-74-3 phenylacetylene 
• 4440-01-1 lithium phenylacetylide 
• 3007-91-8 ethyl-2-naphthoate 
• 932-88-7 1-iodo-2-phenylethyne 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 

Downstream Products

• 16736-88-2 1-(naphthalen-2-yl)-3-phenylprop-2-yn-1-one 
• 1173191-25-7 4-(2-naphthyl)-2-phenyl-4,5,6,7-tetrahydrocyclopenta[b]pyran-5-one 
• 1173191-26-8 C₂₅H₂₀O₂ 
• 1173191-27-9 C₂₇H₂₄O₂ 
• 1254977-17-7 1-phenyl-3H-cyclopenta[a]naphthalene 
• 1383192-97-9 N-benzyloxycarbonyl-3-phenyl-1-(naphthalen-2-yl)-prop-2-yn-1-amine 
• 1567388-28-6 methyl 5-(naphthalen-2-ylmethyl)-4-phenyl-2-(trifluoromethyl)furan-3-carboxylate 
• 4782-69-8 (E)-1-(naphthalen-2-yl)-3-phenylprop-2-en-1-one 
• 1271054-68-2 1-(naphthalen-2-yl)-3-phenylbuta-1,2-diene 

Relevant academic research and scientific papers

Ti-catalyzed regioselective ring-opening alkynylation of epoxides with haloalkynes

Ti-catalyzed ring-opening alkynylation of epoxides with haloalkynes has been achieved, allowing an efficient and regioselective entry to various propargylic alcohols in moderate to good yields. The developed protocol features extremely mild reaction conditions, broad substrate scope, varied functional group compatibility, and chemospecificity in the rearrangements of epoxides to aldehydes.

Straightforward Stereoselective Synthesis of Seven-Membered Oxa-Bridged Rings through in Situ Generated Cycloheptenol Derivatives

An iodine-mediated stereoselective synthesis of seven-membered oxa-bridged rings via in situ generated cycloheptenols was reported. This process was realized through the combination of C-C σ-bond cleavage and C-O bond-forming reactions in a one-pot fashion from simple and easily accessible raw materials. The formation of carbon radicals initiated by I2 was the key to the reaction.

DBU-Catalyzed Rearrangement of Secondary Propargylic Alcohols: An Efficient and Cost-Effective Route to Chalcone Derivatives

A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed rearrangement of diarylated secondary propargylic alcohols to give α,β-unsaturated carbonyl compounds has been developed. The typical 1,3-transposition of oxy functionality, characteristic of Mayer-Schuster rearrangements, is not observed in this case. A broad substrate scope, functional-group tolerance, operational simplicity, complete atom economy, and excellent yields are among the prominent features of the reaction. Additionally, the photophysical properties and crystal-structure-packing behavior of selected compounds were investigated and found to be of interest.

Transition-metal-free C-C σ-bond activation of α-aryl ketones and subsequent Zn-catalyzed intramolecular cyclization: synthesis of tetrasubstituted furans

A highly atom-economical protocol for the synthesis of tetrasubstituted furans has been developed. This process is realized through the tandem reactions of Cs2CO3 promoted C-C σ-bond activation of α-aryl ketones followed by Zn-cataly

Cascade and Effective Syntheses of Functionalized Tellurophenes

A one-pot and transition-metal-catalyst-free synthetic strategy to construct functionalized tellurophenes has been developed. Substituted 1,1-dibromo-1-en-3-ynes are smoothly converted to tellurophenes with telluride salts in high yield via a series of cascade reactions through reductive debromination, hydrotelluration, nucleophilic cyclization, and aromatization. Close inspection of the results clearly showed that the reactivity of in situ prepared telluride salts are significantly influenced by the polarity of the solvent system and the electronic nature of the substituent on the enyne substrate. This method reports the first direct synthesis of 3-aryltellurophenes in high yields at room temperature. This novel reaction strategy is also found to be a promising synthetic method for multisubstituted tellurophenes and selenophenes.

Highly Efficient Synthesis of Multi-Substituted Allenes from Propargyl Acetates and Organoaluminum Reagents Mediated by Palladium

A simple and mild catalytic S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents is reported. The S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents mediated by Pd(PhP 3) 2 Cl 2 (1 mol%)/PPh 3 (2 mol%)/K 2 CO 3 in tetrahydrofuran at 60 °C for 3-4 hours afforded the corresponding multi-substituted allenes in good yields (up to 94%) with high selectivities (up to 99%). The process was simple and easily performed, which offers an efficient method to synthesize the multi-substituted allene derivatives.

Catalytic α-Allylation of Enones with Alcohols via [Gold(I)]-Mediated [3,3]-Sigmatropic Rearrangement of Propargylic Carboxylates

The site-selective α-allylic alkylation of enones with alcohols via gold-triggered formation of nucleophilic allenoates by means of [3,3]-sigmatropic rearrangements of propargylic carboxylates is reported. A range of α-alkylated enones is obtained in high yields in the presence of the gold complex [JohnPhosAu(ACN)]SbF6 (2 mol%) as the promoting agent. Examples of allylation/Friedel-Crafts alkylation sequences are also provided, delivering densely functionalized dihydroindenes and dihydrobenzo[7]annulenes in a one-pot procedure in moderate yields. The role of the Br?nsted acidity (i.e., pivalic acid) delivered during the reaction course in assisting the formation of carbocationic intermediates is documented.

Modulation of silver-titania nanoparticles on polymethylhydrosiloxane-based semi-interpenetrating networks for catalytic alkynylation of trifluoromethyl ketones and aromatic aldehydes in water

In this work, we have developed a new approach to monodispersed hybrid Ag@TiO2 nanocomposites using a titanium-promoted cross-linking reduction in the Si-H functional material, polymethylhydrosiloxane (PMHS)-based semi-interpenetrating networks

Catalytic asymmetric enyne addition to aldehdyes and Rh(I)-catalyzed stereoselective domino Pauson-Khand/[4 + 2] cycloaddition

The 1,1′-bi-2-naphthol-ZnEt2-Ti(OiPr) 4-Cy2NH system is found to catalyze the 1,3-enyne addition to aliphatic aldehydes as well as other aldehydes at room temperature with 75-96% yield and 82-97% ee. This system is also broadly applicable for the highly enantioselective reaction of other alkyl-, aryl-, and silylalkynes with structurally diverse aldehydes. The propargylic alcohols prepared from the catalytic asymmetric enyne addition to aliphatic aldehydes are used to prepare a series of optically active trienynes. In the presence of a catalytic amount of [RhCl(CO)2]2 and 1 atm of CO, the optically active trienynes undergo highly stereoselective domino Pauson-Khand/[4 + 2] cycloaddition to generate optically active multicyclic products. The Rh(I) catalyst is also found to catalyze the coupling of a diyne with CO followed by [4 + 2] cycloaddition to generate an optically active multicyclic product. These transformations are potentially useful for the asymmetric synthesis of polyquinanes containing a quaternary chiral carbon center.

A new and general one-pot synthesis of propargyl alcohols from esters

Intermediates easily prepared by partial reduction of various esters with LDBBA as a reducing agent smoothly react with lithium acetylides to give propargyl alcohols, without isolation of partial reduction intermediates, in good yields (73-83%).