71257-77-7

Upstream product

• 109-72-8 n-butyllithium 
• 865-50-9 iodomethane-d3 
• 536-74-3 phenylacetylene 

Downstream Products

• 1423-07-0 1-deutero-2,3,4,5,6-pentafluorobenzene 

Relevant academic research and scientific papers

Palladium-Catalyzed Dearomative Allylic Alkylation of Indoles with Alkynes to Synthesize Indolenines with C3-Quarternary Centers

A palladium-catalyzed dearomative allylic alkylation of indoles with alkynes to construct indolenines with C3-quarternary centers was reported. The in situ formed arylallene intermediate omitted the need to install leaving groups on the allylic compounds and employ extra oxidants to oxidize the allylic C-H bonds. The reaction exhibited good functional group tolerance and high atom economy. Moreover, the reaction was further expanded to synthesize pyrroloindolines and furanoindolines.

Enantioselective Addition of α-Nitroesters to Alkynes

By using Rh–H catalysis, we couple α-nitroesters and alkynes to prepare α-amino-acid precursors. This atom-economical strategy generates two contiguous stereocenters, with high enantio- and diastereocontrol. In this transformation, the alkyne undergoes isomerization to generate a RhIII–π-allyl electrophile, which is trapped by an α-nitroester nucleophile. A subsequent reduction with In powder transforms the allylic α-nitroesters to the corresponding α,α-disubstituted α-amino esters.

Palladium-Catalyzed Oxidative Synthesis of α-Acetoxylated Enones from Alkynes

We report a palladium-catalyzed oxidative functionalization of alkynes to generate α-acetoxylated enones in one step. A range of functional groups are well-tolerated in this reaction. Mechanistic studies, including the use of 18O-labeled DMSO,

A Correlation between β-Hydrogen Isotope Effects on Carbon-13 NMR Chemical Shifts in Unsaturated Systems and the Strength of Hyperconjugative Interactions

β-Hydrogen isotope effects on the carbon-13 NMR chemical shifts of the trigonal carbon in CL3C(R)=X (L=H, or D) are reported for 15 substances inwhich the positive charge density at the trigonal carbon is regulated through systematic variation of R and X.A linear relationship is found between these isotope effects and the chemical shifts of the trigonal carbons, and this is taken as evidence for dependence of the magnitude of these isotope effects upon the strength of the hyperconjugative interaction between CL3 and C(R)=X.An explanation of hyperconjugative NMR isotope effecs in terms of anharmonic carbon-hydrogen bond-bending vibrations is advanced.

Mechanism, regiochemistry, and stereochemistry of the insertion reaction of alkynes with methyl(2,4-pentanedionato)(triphenylphosphine)nickel. A cis insertion that leads to trans kinetic products

This study reports the rapid reaction under mild conditions of internal and terminal alkynes with methyl(2,4-pentanedionato)(triphenylphosphine)nickel (1) in aromatic and ethereal solvents. In all cases vinylnickel products (2) are formed by insertion of the alkyne into the nickel-methyl bond. The regiochemistry is unusual; unsymmetrical alkynes give selectively the one regioisomer with the sterically largest substituent next to the nickel atom. So that the stereochemistry of the initial insertion could be investigated, an X-ray diffraction study of the reaction of 1 and diphenylacetylene was carried out. This showed that the vinylnickel complex formed by overall trans insertion was the product of the reaction. Furthermore, subsequent slow isomerization of this complex, to a mixture of it and the corresponding cis isomer, demonstrated that this trans addition product is the kinetic product of the reaction. In studies with other alkynes, the product of trans addition was not always exclusively (or even predominantly) formed, but the ratio of the stereoisomers formed kinetically was substantially different from the thermodynamic ratio. Isotope labeling, added phosphine, and other experiments have allowed us to conclude that the mechanism of this reaction does involve cis addition. However, a coordinatively unsaturated vinylnickel intermediate is initially formed, which can undergo rapid, phosphine-catalyzed cis-trans isomerization in competition with its conversion to the isolable phosphine-substituted products.