18215-68-4

Upstream product

• 109-65-9 1-bromo-butane 
• 3923-52-2 1,1-diphenyl-2-propyn-1-ol 
• 119-61-9 benzophenone 
• 218793-76-1 triethoxy(hex-1-yn-1-yl)silane 
• 693-02-7 hex-1-yne 
• 106-38-7 para-bromotoluene 

Downstream Products

• 951403-52-4 1,1-diphenylhept-2-ynyl acetate 
• 1263145-89-6 1-butyl-9-methyl-3,3-diphenyl-3H-pyrrolo[1,2-a]indole 
• 1311196-94-7 3-butyl-4-(diphenylmethylene)-5-phenyl-1-(phenylsulfonyl)-4,5-dihydro-1H-pyrazole 
• 1379964-41-6 C₂₅H₃₆OSi 
• 1379963-90-2 C₂₅H₃₆OSi 
• 1415035-10-7 3-butyl-5,5-diphenyl-2-tosyl-2,5-dihydroisoxazole 
• 1415035-25-4 3-butyl-4-iodo-5,5-diphenyl-2-tosyl-2,5-dihydroisoxazole 
• 1418213-88-3 C₃₆H₃₁NO₃ 
• 105532-96-5 5-butyl-3,4-diphenyl-1H-pyrazole 

Relevant academic research and scientific papers

Chiral Bifunctional Phosphine Ligand Enabling Gold-Catalyzed Asymmetric Isomerization of Alkyne to Allene and Asymmetric Synthesis of 2,5-Dihydrofuran

The asymmetric isomerization of alkyne to allene is the most efficient and the completely atom-economic approach to this class of versatile axial chiral structure. However, the state-of-the-art is limited to tert-butyl alk-3-ynoate substrates that possess

Synthesis and Photochemistry of a New Photolabile Protecting Group for Propargylic Alcohols

A new and efficient thiochromenone S,S-dioxide-based photolabile protecting group for propargylic alcohols is described. Robust protection reactions were developed through copper (II)-catalyzed substitution of propargylic alcohols. Subsequent photodeprote

Cadmium(II) Chloride-Catalyzed Dehydrative C?P Coupling of Propargyl Alcohols with Diarylphosphine Oxides to Afford Allenylphosphine Oxides

The cadmium(II) chloride-catalyzed dehydrative C?P cross-coupling reaction of propargyl alcohols with diarylphosphine oxides is reported. Several propargyl alcohols including those bearing the sterically demanding tert-butyl group at the triple bond terminus can be used as good substrates in the reaction to produce the corresponding allenylphosphine oxides in good to high yields in acetonitrile at 100 °C. The reaction can also be easily scaled up to a gram-scale synthesis. A mechanism study indicates that the reaction may proceed through a process of propargylic substitution to generate phosphonite intermediates followed by [2,3] sigmatropic rearrangement to produce the allenyl products, rather than through a common allenylative substitution resulting from P-nucleophilicity. (Figure presented.).

Regioselective rapid synthesis of fully substituted 1,2,3-triazoles mediated by propargyl cations

Regioselective rapid triazole syntheses at low temperature are described. Organic azides and propargyl cations generated by acids gave fully substituted 1H-1,2,3-triazoles. Most reactions could be performed in 5 min at not only rt but also -90 C. Both terminal and internal alkynes were acceptable, and the sterically bulky substituents could afford the products smoothly. Various types of three-component coupling reactions were demonstrated, and the presence of allenylaminodiazonium intermediates was indicated.

Platinum-catalyzed hydrosilylations of internal alkynes: Harnessing substituent effects to achieve high regioselectivity

Rule of thumb: The high yielding title reaction is described with a focus on understanding the factors that govern the regioselectivity of the process (see scheme). Electronic, steric, and functional group properties all influence the selectivity, an understanding of which allows the selective formation of trisubstituted vinylsilanes, which are synthetically useful compounds for accessing stereodefined alkenes. Copyright

One-pot consecutive reactions based on the synthesis of conjugated enones by the re-catalysed meyer-schuster rearrangement

Re catalysis in one-pot reactions: An atom-economical, one-pot strategy that involves alkyne deprotonation and a subsequent rhenium(V)-catalysed Meyer-Schuster rearrangement of the alkynol to provide α,β- unsaturated enones in high yield has been developed (see scheme). Subsequent in situ hydride reduction or Diels-Alder reaction of the enones provided products in good-to-high overall yields. Copyright

Efficient synthesis of di- and trisubstituted 2-aryloxazoles via ytterbium(III) triflate catalyzed cyclization of tertiary propargylic alcohols with aryl amides

An efficient synthetic method to prepare di- and trisubstituted 2-aryloxazoles based on Yb(OTf)3 catalyzed cyclization of trisubstituted propargylic alcohols with aryl amides is described. The reaction was accomplished in moderate to excellent product yields and with complete regioselective control. The mechanism is suggested to involve activation of the starting alcohol by the metal catalyst that results in its ionization. Subsequent cyclization of this newly generated carbocationic species with the aryl amide then affords the oxazole. In view of the mild conditions along with the low cost, commercially availability of Yb(OTf)3 and its high tolerance to air and moisture, the present synthetic approach offers an operationally simplistic and convenient route to this important aromatic heterocycle.

Tandem reaction of propargyl alcohol and N-sulfonylhydrazone: Synthesis of dihydropyrazole and its utility in the preparation of 3,3-diarylacrylonitrile

An efficient and straightforward strategy for the synthesis of 4-methylene-1-(phenylsulfonyl)-4,5-dihydro-1H-pyrazole from propargyl alcohol and N-sulfonylhydrazone is described. N-Sulfonyl allenamide is postulated to be the key intermediate for this tandem transformation.

Bronsted acid catalyzed cyclization of propargylic alcohols with thioamides. Facile synthesis of Di- and trisubstituted thiazoles

Figure presented. A general and efficient method to prepare 2,4-di- and trisubstituted thiazoles via p-TsOH·H2O-catalyzed cyclization of trisubstituted propargylic alcohols with thioamides is described. The reaction was accomplished in moderate to excellent product yields under mild conditions that did not require the exclusion of air and moisture and offers an operationally simplistic and convenient route to this synthetically useful aromatic heterocycle.

Ytterbium(III) triflate catalyzed tandem friedel-crafts alkylation/hydroarylation of propargylic alcohols with phenols as an expedient route to indenols

A method to prepare indenols efficiently by ytterbium(III) triflate catalyzed tandem Friedel - Crafts alkylation/hydroarylation of propargylic alcohols with phenols is described. The reaction was accomplished In moderate to excellent yields and regioselectivity under mild conditions and offers a straightforward and convenient one step synthetic route to bioactive indenols and its derivatives.