312329-85-4

Upstream product

• 1252671-79-6 1-ethynyl-1,2-benziodoxol-3(1H)-one 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 1433138-98-7 N-allyl-4-methyl-N-((trimethylsilyl)ethynyl)benzenesulfonamide 
• 593-61-3 bromoethyne 
• 945536-26-5 4-methyl-N-2-propen-1-yl-N-[2-[tris(1-methylethyl)silyl]ethynyl]-benzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 312329-89-8 N-allyl-N-(2,2-dibromovinyl)-4-methyl-benzenesulfonamide 
• 312329-75-2 N-allyl-N-formyl-4-methyl-benzenesulfonamide 

Downstream Products

• 349458-90-8 N-allyl-4-methyl-N-[(E)-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-propenyl]-4-benzenesulfonamide 
• 1017581-45-1 C₁₉H₁₈N₂O₃S 
• 1538596-03-0 N-allyl-N-(1-chlorovinyl)-4-methylbenzenesulfonamide 
• 1585210-02-1 N-allyl-N-(4-phenylbuta-1,3-diyn-1-yl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Copper-Catalyzed Synthesis of Terminal vs. Fluorine-Substituted N-Allenamides via Addition of Diazo Compounds to Terminal Ynamides

A copper-mediated coupling reaction between ynamides and diazo-compounds to produce N-allenamides is reported for the first time. This method enables facile and rapid access to terminal N-allenamides by using commercially available TMS-diazomethane with w

Catalytic Asymmetric Hydroacyloxylation/Ring-Opening Reaction of Ynamides, Acids, and Aziridines

A highly enantioselective three-component reaction of ynamides with carboxylic acids and 2,2′-diester aziridines has been realized by using a chiral N,N′-dioxide/Ho(OTf)3 complex as a Lewis acid catalyst. The process includes the formation of an α-acyloxyenamide intermediate through the addition of carboxylic acids to ynamides and the following enantioselective nucleophilic addition to in-situ-generated azomethine ylides induced by the chiral catalyst. A range of amino acyloxyenamides are delivered in moderate to good yields with good ee values. In addition, a possible catalytic cycle with a transition model is proposed to elucidate the reaction mechanism.

Direct Synthesis of CF2H-Substituted 2-Amidofurans via Copper-Catalyzed Addition of Difluorinated Diazoacetone to Ynamides

The significance of molecules containing difluoromethyl groups is driven by their potential applications in pharmaceutical and agrochemical science. Methods for the incorporation of lightly fluorinated groups such as CF2H have been less well developed. He

Metal-free C8-H functionalization of quinolineN-oxides with ynamides

The metal-free C8-H functionalization of quinolineN-oxides with ynamides is unveiled for the first time by the intramolecular Friedel-Crafts-type reaction of quinolyl enolonium intermediates generated from Br?nsted acid-catalyzed addition of quinolineN-ox

Catalytic Asymmetric Three-component Hydroacyloxylation/ 1,4-Conjugate Addition of Ynamides

A highly enantioselective three-component hydroacyloxylation/1,4-conjugate addition of ortho-hydroxybenzyl alcohols, ynamides and carboxylic acids was developed under mild reaction conditions in the presence of a chiral N,N′-dioxide/Sc(OTf)3 complex, which went through in situ generated ortho-quinone methides with α-acyloxyenamides, delivering a range of corresponding chiral α-acyloxyenamides derivatives containing gem(1,1)-diaryl skeletons in moderate to good yields with excellent ee values. The scale-up experiment and further derivation showed the practicality of this catalytic system. In addition, a possible catalytic cycle and transition state model was proposed to elucidate the origin of the stereoselectivity based on X-ray crystal structure of the α-acyloxyenamide intermediate and product.

Gold(III)-catalyzed chemoselective annulations of anthranils with N-allylynamides for the synthesis of 3-azabicyclo[3.1.0]hexan-2-imines

We herein report the gold(iii)-catalyzed selective annulation of anthranils with N-allylynamides under mild conditions. By trapping the in situ-generated α-imino gold carbenes, 3-azabicyclo[3.1.0]hexan-2-imines were obtained in high synthetic efficiency. The reaction, which can be conducted in the gram scale, tolerates electron-rich and electron-deficient anthranils as well as a diverse set of functionalized ynamides (aryl- and alkyl-substituted terminal).

Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex

The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.

Chemoselective alkynylation of N-sulfonylamides versus amides and carbamates-Synthesis of tetrahydropyrazines

The chemoselective alkynylation of N-sulfonylamides versus amides and carbamates using TMS-EBX as an alkynylating agent leads to the formation of non-symmetrical tetrahydropyrazines from orthogonally protected diamines. The Royal Society of Chemistry 2013

Palladium-mediated [2+1] cycloaddition of norbornene derivatives with ynamides

An efficient palladium-catalyzed [2+1] cycloaddition between ynamides and norbornenes or norbornadienes is reported. Both phosphapalladacycles and palladium/secondary phosphine oxide catalytic systems were found to be competent for the transformation allowing the preparation of aminomethylenecyclopropanes. The reaction showed general applicability to various functionalized bicyclo[2.2.1]hept-2-enes and ynamides. A chiral phosphapalladacycle was tested to carry out this transformation in an enantioselective fashion.

Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes

Rh(I) carbenes were conveniently generated from readily available ynamides. These metal carbene intermediates could undergo metathesis with electron-rich or neutral alkynes to afford 2-oxopyrrolidines or be trapped by tethered alkenes to yield 3-azabicyclo[3.1.0]hexanes, a common skeleton in numerous bioactive pharmaceuticals. Although the scope of the former is limited, the latter reaction tolerates various substituted alkenes.