87446-02-4

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 536-74-3 phenylacetylene 
• 433292-22-9 3-(trimethylsilyl)-1-(pyridin-3-yl)prop-2-yn-1-ol 
• 276884-35-6 3-hydroxy-3-(3-pyridinyl)-1-propyne 
• 591-50-4 iodobenzene 

Downstream Products

• 1017682-00-6 1-(3-phenyl-1-(pyridin-3-yl)prop-2-ynyl)-1 acetate 
• 1017682-02-8 3-(3-phenylprop-2-ynyl)pyridine 
• 86535-76-4 3-phenyl-1-(pyridin-3-yl)prop-2-yn-1-one 

Relevant academic research and scientific papers

InBr3-Et3N promoted alkynylation of aldehydes and N,O-acetals under mild conditions: Facile and simple preparation of propargylic alcohols and amines

The use of a novel InBr3-Et3N reagent system to promote addition reactions of 1-alkynes not only with a variety of aromatic or bulky aliphatic aldehydes but also with N,O-acetals is described. The corresponding propargylic alcohols or amines are produced in good to excellent yields.

Redox-Neutral Arylations of Vinyl Cation Intermediates

Herein we present a new unified concept for C?C bond formation under redox-neutral conditions. Our strategy hinges upon interception of a vinyl cation with a sulfoxide resulting in simultaneous C–C and C?O bond formation and arylation. A range of structurally diverse vinyl cations are generated in situ in the presence of a sulfoxide, resulting in hydrative arylation, direct arylation of enol triflates and interrupted Meyer–Schuster rearrangement. Mechanistic investigations showcase the crucial role played by the fleeting vinyl cation intermediate and structural features that lead to its stabilization. Applications of the reaction products to synthesis are also presented. (Figure presented.).

Spiroannulation of Oxindoles via Aryne and Alkyne Incorporation: Substituent-Diverted, Transition-Metal-Free, One-Pot Access to Spirooxindoles

A "product control via substrate design" strategy has been conceptualized and implemented to harness the potential of aryne and activated alkyne insertions into oxindoles to readily and efficiently furnish pharmacophoric indano- and cyclopentannulated spirooxindole scaffolds in an operationally straightforward, one-pot, transition-metal-free protocol.

Enabling Asymmetric Alkynylation of Azaaryl Aldehydes with Soai Autocatalyst

A new sequence of autocatalysis-catalysis in asymmetric alkynylation of azaaryl aldehydes in the presence of Soai (5-pyrimidyl)alkanol as chiral catalyst is documented. The autocatalyst can be generated from almost racemic environment to up to 99.5% ee an

Base-mediated cascade rearrangements of aryl-substituted diallyl ethers

Two base-mediated cascade rearrangement reactions of diallyl ethers were developed leading to selective [2,3]-Wittig-oxy-Cope and isomerization-Claisen rearrangements. Both diaryl and arylsilyl-substituted 1,3-substituted propenyl substrates were examined, and each exhibits unique reactivity and different reaction pathways. Detailed mechanistic and computational analysis was conducted, which demonstrated that the role of the base and solvent was key to the reactivity and selectivity observed. Crossover experiments also suggest that these reactions proceed with a certain degree of dissociation, and the mechanistic pathway is highly complex with multiple competing routes.

NaH mediated isomerisation-allylation reaction of 1,3-substituted propenols

A base mediated isomerisation-allylation protocol of 1,3-disubstituted propenols has been established. The use of diaryl and aryl-silyl substrates is reported alongside the use of substituted allyl bromides. Mechanistic experiments have also been conducted to elucidate the reaction pathway. The Royal Society of Chemistry 2013.

Solvent-free synthesis of propargylic alcohols using zno as a new and reusable catalyst by direct addition of alkynes to aldehydes

Under solvent-free conditions, the synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes promoted by ZnO as a novel, commercially, and cheap catalyst is described. Furthermore, the catalyst can be reused for several times w

The synthesis of highly substituted isoxazoles by electrophilic cyclization: An efficient synthesis of valdecoxib

(Chemical Equation Presented) A large number of functionally substituted 2-alkyn-1-one O-methyl oximes have been cyclized under mild reaction conditions in the presence of ICl to give the corresponding 4-iodoisoxazoles in moderate to excellent yields. The resulting 4-iodoisoxazoles undergo various palladium-catalyzed reactions to yield 3,4,5-trisubstituted isoxazoles, including valdecoxib.

Synthesis of pentafluorophenyl- and pyridinyl-3 allenes

The allenes 1,2,3,4,5-pentafluoro-6-(3-phenylpropa-1,2-dienyl)benzene 4, 3-(3-phenylpropa-1,2-dienyl)pyridine 11 and 3-(3-(pyridine-3-yl)propa-1,2- dienyl)pyridine 17 and the acetylenes 5, 12 and 16 were obtained by reduction of the corresponding propargy

Facile and convenient synthesis of functionalized propargylic alcohols and amines: An InBr3-Et3N reagent system promotes the alkynylation of aldehydes and N,O- or N,S-acetals

The use of a novel InBr3-Et3N reagent system to promote the alkynylation of not only a variety of aromatic/heterocyclic or bulky aliphatic aldehydes but also N,O- or N,S-acetals is described. The use of N-silyl-N,O-acetals and 1-alkynes could lead to the direct production of primary propargylic amines in good yields.