30265-81-7

Usage

Physical state

Colorless to pale yellow liquid

Odor

Mild aromatic

Uses

a. Building block in the synthesis of pharmaceuticals
b. Building block in the synthesis of agrochemicals
c. Building block for other organic compounds
d. Production of advanced materials
e. Reagent in organic chemistry

Safety

Flammable, requires proper handling and safety precautions

Upstream product

• 3218-36-8 4-Phenylbenzaldehyde 
• 1066-54-2 trimethylsilylacetylene 
• 4301-14-8 acetylenemagnesium bromide 
• 70277-75-7 lithium acetylide 

Downstream Products

• 1221747-54-1 C₂₅H₁₈O 
• 1429048-94-1 methyl 2-([1,1'-biphenyl]-4-yl)pyrrolo[1,2-b]pyridazine-7-carboxylate 

Relevant academic research and scientific papers

Iridium-Catalyzed Enantioselective and Chemodivergent Allenylic Alkylation of Vinyl Azides for the Synthesis of α-Allenylic Amides and Ketones**

The first enantioselective synthesis of α-allenylic amides and ketones through allenylic alkylation of vinyl azides is reported. In these chemodivergent reactions, cooperatively catalyzed by a IrI/(phosphoramidite,olefin) complex and Sc(OTf)3, vinyl azides act as the surrogate for both amide enolates and ketone enolates. The desiccant (molecular sieves) plays a crucial role in controlling the chemodivergency of this enantioconvergent and regioselective reaction: Under otherwise identical reaction conditions, the presence of the desiccant led to α-allenylic amides, while its absence resulted in α-allenylic ketones. Utilizing racemic allenylic alcohols as the alkylating agent, the overall process represents a dynamic kinetic asymmetric transformation (DyKAT), where both the products are formed with the same absolute configuration. To the best of our knowledge, this is the first example of the use of vinyl azide as the ketone enolate surrogate in an enantioselective transformation.

Multisubstituted pyrazole synthesis via [3?+?2] cycloaddition/rearrangement/N[sbnd]H insertion cascade reaction of α-diazoesters and ynones

The cascade reactions of alkyl α-diazoesters and ynones using Al(OTf)3 as the catalyst are described. A series of 4-substituted pyrazoles were obtained via [3 + 2] cycloaddition, 1,5-ester shift, 1,3-H shift, and N[sbnd]H insertion process. Deuterium labelling experiments, kinetic studies and control experiments were carried out for the rationalization of the mechanism.

Axial-to-Central Chirality Transfer for Construction of Quaternary Stereocenters via Dearomatization of BINOLs

All-carbon quaternary stereocenters are versatile building blocks, and their asymmetric construction has attracted much attention. Herein, we disclose an axial-to-central chirality transfer strategy for the synthesis of chiral quaternary stereocenters via dearomatization of (S)-BINOLs. The reaction proceeded smoothly with a wide range of propargyl carbonates to afford chiral spiro-compounds in high yields with excellent enantioselectivities. In addition, the strategy was extended to kinetic resolution of rac-BINOLs albeit with moderate s value.

Regioselectivity Switch in Palladium-Catalyzed Allenylic Cycloadditions of Allenic Esters: [4+1] or [4+3] Cycloaddition/Cross-Coupling

The first Pd-catalyzed asymmetric allenylic [4+1] cycloaddition was successfully developed. Alternatively, tuning the Pd catalyst switched the reactivity toward an unprecedented [4+3] cycloaddition/cross-coupling. Ligands play a vital role in controlling the reaction pathway, allowing highly selective access to different products from identical substrates. Biological evaluation of the obtained compounds led to the discovery of new antitumor targets. A possible mechanism is proposed, suggesting two interesting catalytic cycles for the cycloaddition with palladium-butadienyls. This study also demonstrated the potential and utility of allenic esters as 1,4-biselectrophiles and C4 synthons for participating in cycloaddition reactions.

Allenylic Carbonates in Enantioselective Iridium-Catalyzed Alkylations

An enantioconvergent C(sp3)-C(sp3) coupling between racemic allenylic electrophiles and alkylzinc reagents has been developed. An Ir/(phosphoramidite,olefin) catalyst provides access to highly enantioenriched allenylic substitution p

Gem-Digold Acetylide Complexes for Catalytic Intermolecular [4 + 2] Cycloaddition: Having Two Gold Centers Is Better for Asymmetric Catalysis

Gold(I)-catalyzed highly enantioselective intermolecular [4 + 2] cycloaddition is shown with ynones and cyclohexadiene. Various bicyclo[2.2.2]octadiene derivatives are produced in high yields (up to 99%) with good enantioselectivity (up to 96% ee). Key to the success is generation of the gem-digold terminal alkyne as a catalytic on-cycle species. As proof of the gem-digold catalysis, a positive nonlinear effect is clarified between the ee's of the ligand and the cycloadduct.

Gold-Catalyzed Dehydrogenative Cycloisomerization of 1,4-Enyne Esters to 3,5-Disubstituted Phenol Derivatives

A method to prepare synthetically important 3,5-disubstituted phenol derivatives that relies on the sequential gold(I)-catalyzed dehydrogenative cycloisomerization of 1,4-enyne esters in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) or N-fluorobenzenesulfonimide (NFSI) is described. The synthetic versatility of the methodology was exemplified by a gram-scale reaction of one example, the ease to realize subsequent functional transformations of an adduct, and the application of the method to the synthesis of the bioactive molecule LUF5771. (Figure presented.).

Parallel synthesis of "Click" chalcones as antitubulin agents

It has been shown that some chalcones are able to inhibit tubulin polymerization, giving cytotoxicity and destruction of tumoral vasculature. A library of 180 novel chalcone analogs has been synthesized via click chemistry and screened for their cytotoxic

Remarkable high-yielding chemical modification of gold nanoparticles using uncatalyzed click-type i ,3-dipolar cycloaddition chemistry and hyperbaric conditions

Azide-terminated alkyl thiolate monolayer-protected gold nanoparticles (1-C,12MPN) with a core size of 1.8 ± 0.2 nm were prepared. 1-C,12MPN was modified in high yields via an uncatalyzed 1,3-dipolar cycloaddition (clicktype reaction) with a variety of terminal acyl alkynes under hyperbaric conditions at 11 000 atm. The resulting 1,2,3-tria- zole modified MPNs (2-C,12MPN) were characterized using 1H NMR spectroscopy and were verified by comparison of the spectra to those obtained for the products of the model reactions of 1-azidododecane with the same alkynes. TEM analysis showed that the high-pressure conditions did not affect the size of the gold core, suggesting that the only effect is to facilitate the chemical reaction on the particles.

Copper-catalyzed asymmetric propargylic substitution reactions of propargylic acetates with amines

(Chemical Equation Presented) Flexing your bipheps: Enantioselective propargylic substitution reactions of propargylic acetates with amines catalyzed by a copper-(R)-Cl-MeO-biphep or -binap complex give the corresponding propargylic amines in excellent yi