153395-93-8

Upstream product

• 637-87-6 1-Chloro-4-iodobenzene 
• 2028-63-9 but-3-yn-2-ol 
• 64-17-5 ethanol 
• 33491-03-1 1-(bromoethynyl)-4-chlorobenzene 
• 873-73-4 4-n-chlorophenylacetylene 
• 75-07-0 acetaldehyde 
• 153395-92-7 2-tetrahydropyranyloxy-4-(p-chlorophenyl)-3-butyne 
• 106-39-8 bromochlorobenzene 
• 39180-26-2 4-(4-chlorophenyl)-3-butyn-2-one 

Downstream Products

• 1188375-76-9 4-(p-chlorophenyl)-4-iodo-3-(n-pentyl)-3(Z)-buten-2-ol 
• 153395-94-9 1-(3-bromobut-1-yn-1-yl)-4-chlorobenzene 
• 1450831-23-8 C₁₁H₈ClF₃ 
• 1450831-19-2 C₁₀H₈Cl₂ 
• 1393376-11-8 C₂₁H₁₉ClO 
• 39180-26-2 4-(4-chlorophenyl)-3-butyn-2-one 
• 944819-14-1 2-[3-(4-chloro-phenyl)-1-methyl-prop-2-ynyl]-isoindole-1,3-dione 
• 6302-55-2 1-(4'-chlorophenyl)-1,3-butanedione 

Relevant academic research and scientific papers

Silver Mediated Banert Cascade with Carbon Nucleophiles

The Banert cascade of propargylic azides can be promoted by simple silver salts, and the triazafulvene intermediate can be intercepted by carbon nucleophiles. Various indoles (>25 examples, up to 92% yield) and electron-rich heterocycles were effective. T

Intercepting the Banert cascade with nucleophilic fluorine: Direct access to α-fluorinated: N H-1,2,3-triazoles

The treatment of propargylic azides with silver(i) fluoride in acetonitrile was found to yield α-fluorinated NH-1,2,3-triazoles via the Banert cascade. The reaction was regioselective and the products result from an initial [3,3] rearrangement. The reacti

Synthesis of Highly Substituted Biaryls by the Construction of a Benzene Ring via in Situ Formed Acetals

Herein, we present an interesting method for the construction of a benzene ring using propargylic alcohols and 1,3-dicarbonyls, which involves three new C-C bond formations via cascade alkylation, formylation, annulation, and aromatization to make substituted biaryls. This one-pot Br?nsted acid-promoted protocol utilizes the unique reactivity of the acetal formed under the reaction conditions. Alkynyl methyl ketones could be employed instead of 1,3-dicarbonyls as they are converted to 1,3-dicarbonyls by hydration under the reaction conditions.

Divergent Mechanisms of the Banert Cascade with Propargyl Azides

Triazoles are privileged heterocycles for a variety of applications. The synthesis of 1H-triazoles can be accomplished by the Banert cascade from propargylic azides. Depending on the substrate and conditions, the Banert cascade can proceed by either a sigmatropic or prototropic mechanism. This report describes the first detailed kinetic analysis of the Banert cascade proceeding by both pathways including substituent effects and KIE. The analysis identified the inflection point in the divergent pathways, allowing future work to predict which Banert products are accessible.

Synthesis of substituted benzo[: B] [1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones

We have developed a novel synthetic method accessing benzo[b][1,4]oxazepines that are one of the rare classes of benzoxazepine derivatives by reaction of 2-aminophenols with alkynones in 1,4-dioxane at 100 °C. A series of benzo[b][1,4]oxazepine derivatives can be prepared by using this synthetic protocol. Mechanistic experiments indicated that the hydroxy proton of the aminophenol could play a crucial role in the formation of an alkynylketimine intermediate that undergoes 7-endo-dig cyclization.

Transition-Metal-Free Synthesis of Electron Rich 1,3-Dienes via Base Promoted Isomerization of Propargylic Ethers

Herein, a novel and scalable synthesis of electron rich 1,3-dienes based on KOtBu mediated isomerization of propargylic ether derivatives was developed. This new process features easy handling reaction conditions, transition-metal-free isomerization, high isolated yields, and most of all, it could be used for modification of natural products at late stage functionalizations.

Kinetic Resolution of Propargylic Ethers via [2,3]-Wittig Rearrangement to Synthesize Chiral α-Hydroxyallenes

An efficient kinetic resolution of propargyloxy dicarbonyl compounds via asymmetric [2,3]-Wittig rearrangement was achieved by using a chiral N,N′-dioxide/NiII complex catalyst. Various chiral α-allenyl alcohols were obtained in high enantioselectivities under mild conditions. The utility of this method was readily demonstrated in the asymmetric synthesis of the chiral 2,5-dihydrofuran derivative.

Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: Synthesis of propargyl alcohols and α-ketoesters

The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N2 or O2). A N2 atmosphere favours propargyl alcohols via a direct C-C coupling process, whereas an O2 atmosphere results in the generation of α-ketoesters through the oxidative CC/C-O coupling pathway.

Phosphine-Catalyzed Intermolecular Annulations of Fluorinated ortho-Aminophenones with Alkynones – The Switchable [4+2] or [4+2]/[3+2] Cycloaddition

A phosphine-catalyzed intermolecular annulation reaction of functionalized ortho-aminoacetophenones with alkynones has been disclosed in this paper. A variety of 2-alkynylquinolines and benzo-fused indolizine were selectively afforded in moderate to good yields at different reaction temperatures and with different phosphine catalysts via the in situ generated zwitterionic intermediate derived from alkynone and phosphine. (Figure presented.).

Nickel-Catalyzed Directed Hydroarylation of Alkynes with Boronic Acids

A regio- and stereoselective nickel-catalyzed hydroarylation of alkynes using propargylic carbamates as directing groups has been developed. The reaction proceeds under mild reaction conditions using arylboronic acids in the absence of base. A range of heterocycles and functional groups are tolerated under the reaction conditions, providing high yields of trisubstituted alkenes with control of olefin geometry.