229015-31-0

Upstream product

• 455-13-0 4-Iodobenzotrifluoride 
• 2028-63-9 but-3-yn-2-ol 
• 705-31-7 4-trifluoromethylphenylacetylene 
• 75-07-0 acetaldehyde 
• 681432-15-5 4-[4-(trifluoromethyl)phenyl]but-3-yn-2-one 
• 402-43-7 p-trifluoromethylphenyl bromide 

Downstream Products

• 205108-16-3 1-(buta-1,2-dien-1-yl)-4-(trifluoromethyl)benzene 
• 1334158-45-0 (Z)-3-phenyl-4-(4-(trifluoromethyl)phenyl)but-3-en-2-ol 
• 681432-15-5 4-[4-(trifluoromethyl)phenyl]but-3-yn-2-one 

Relevant academic research and scientific papers

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.

An efficient nanocluster catalyst for Sonogashira reaction

Pd together with CuI has been well known as the catalyst towards Sonogashira reaction, which provides an effective route to functional alkynes. However, the achievement of high activity and selectivity of this catalytic system is still challenging in some cases. Illustrative examples include their low activity for aryl chloride substrates, and switched selectivity to oxidative coupling products in air atmosphere. In this work, a Cu-incorporated Au13 nanocluster [Au13Cu2(PPh3)6(SC2H4Ph)6]+[NO3]- (Au13Cu2) was designed and prepared in high yield via rapid synthesis. This atomically precise nanocluster shows the potential to be a novel catalytic system for Sonogashira reaction, featuring high activity and selectivity, as well as good recyclability even in air atmosphere.

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

Aromatic Aza-Claisen Rearrangement of Arylpropargylammonium Salts Generated in situ from Arynes and Tertiary Propargylamines

The charge-accelerated aza-Claisen rearrangement of ammonium salts serves as a key step in the construction of complex nitrogen-containing molecules. However, much less attention has been paid to the aromatic aza-Claisen rearrangement than to the aliphatic one. Herein, we report an unprecedented aromatic aza-Claisen rearrangement of arylpropargylammonium salts, generated in situ from arynes and tertiary propargylamines, delivering structurally diverse 2-propargylanilines in moderate to good yields with high regioselectivity. This rearrangement proceeds in the absence of strong bases or transition metals, is compatible with moisture and air, tolerates a wide variety of functional groups, and is amenable to forming 11- to 13-membered heterocycles with a triple bond. The 2-propargylaniline products were treated with aluminum chloride in ethanol to afford multisubstituted indoles in moderate to excellent yields. Finally, a series of deuterium-labeling experiments was performed to elucidate the reaction mechanism.

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.

Nickel-Catalyzed Asymmetric Friedel-Crafts Propargylation of 3-Substituted Indoles with Propargylic Carbonates Bearing an Internal Alkyne Group

The nickel-catalyzed highly enantioselective Friedel-Crafts propargylation of 3-substituted indoles with propargylic carbonates bearing an internal alkyne group was developed. A wide array of the propargylic carbonates as well as 3-substituted indoles can be applicable to the asymmetric nickel catalysis, providing the corresponding chiral C-3 propargylated indolenine derivatives bearing two vicinal chiral centers in up to 89% yield with up to >99% ee and 94:6 dr (24 examples).

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.

Chemoselective Luche-Type Reduction of α,β-Unsaturated Ketones by Magnesium Catalysis

The chemoselective reduction of α,β-unsaturated ketones by use of an economic and readily available Mg catalyst has been developed. Excellent yields for a wide range of ketones have been achieved under mild reaction conditions, short times, and low catalyst loadings (0.2-0.5 mol %).

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.