496922-59-9

Upstream product

• 38761-67-0 1-bromo-1-octyne 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 100-46-9 benzylamine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1092383-35-1 N-benzyl-2-oxo-N-tosyloctanamide 
• 1116153-74-2 N-benzyl-N-[(Z)-2-(4-methoxyphenylsulfanyl)-1-octenyl]-p-toluenesulfonamide 
• 1116153-71-9 N-benzyl-N-[(Z)-2-(pentafluorophenylsulfanyl)-1-octenyl]-p-toluenesulfonamide 
• 1116153-57-1 N-benzyl-N-[(Z)-2-(phenylsulfanyl)-1-octenyl]-p-toluenesulfonamide 
• 1116153-70-8 N-benzyl-N-[(Z)-2-(4-bromophenylsulfanyl)-1-octenyl]-p-toluenesulfonamide 
• 1187370-54-2 (E)-N-benzyl-N'-phenyl-N-tosyloctanimidamide 
• 1311313-27-5 N,N'-(2-hexyl-4-pentylcyclopenta-1,4-diene-1,3-diyl)bis(N-benzyl-4-methylbenzenesulfonamide) 
• 1422721-77-4 (E)-N-benzyl-N-(1-bromooct-1-enyl)-4-methylbenzenesulfonamide 
• 1476064-86-4 2-hexyl-3-(N-benzyl-N-(methoxycarbonyl))-2-cyclobuten-1-one 
• 1476064-89-7 2-hexyl-3-(N-benzyl-N-(diethoxyphosphoryl))-2-cyclobuten-1-one 

Relevant academic research and scientific papers

Keteniminium-Driven Umpolung Difunctionalization of Ynamides

A three-component Pd-catalyzed coupling of ynamides, aryl diazonium salts, and aryl boronic acids for the synthesis of novel triaryl-substituted enamides is described. This transformation represents the first example of an umpolung regioselective unsymmetrical syn-1,2-diarylation/aryl-olefination of ynamides. The aryl moieties of the diazonium salt (electrophile) and boronic acid (nucleophile) are explicitly incorporated in the electrophilic α- and nucleophilic β-position, respectively, of the ynamide, resulting in a single isomer of the N-bearing tetrasubstituted olefin. The scope is broad (68 examples), showing excellent functional-group tolerance. DFT calculations substantiate the rationale of the mechanistic cycle and the regioselectivity. The chemoselectivity and synthetic potential of the enamide products were also studied.

Stereoselective Synthesis of Pyrido- and Pyrrolo[1,2-c][1,3]oxazin-1-ones via a Nucleophilic Addition-Cyclization Process of N,O-Acetal with Ynamides

An efficient asymmetric approach to access functionalized pyrido- and pyrrolo[1,2-c][1,3]oxazin-1-ones has been developed through a nucleophilic addition-cyclization process of N,O-acetal with ynamides. A number of substituted ynamides 8a-8o and 3-silyloxypyrrolidine or piperidine N,O-acetals 6a, 7 were amenable to this transformation, and the desired products 9a-9o, 10a-10m were obtained with excellent regioselectivities and outstanding diastereoselectivities. Moreover, chiral ynamides 14a-14f could also experience this addition-cyclization process to afford products 15a-15f in excellent yields.

Gold-Catalyzed syn-1,2-Difunctionalization of Ynamides via Nitrile Activation

Developed is an unprecedented Au(I)-catalyzed syn-1,2-difunctionalization of ynamides with 2-aminobenzonitriles via nitrile activation. The coupling between ynamides and 2-aminobenzonitriles is explicitly regioselective, providing a straightforward access to 2,4-diamino-substituted quinolines. Density functional theory (DFT) study provides insightful information and rationalizes the reaction pathway. It shows how the synergy between ynamide π-activation and nitrile σ-coordination by the Au(I) catalyst makes the cyclization viable.

Yttrium-catalyzed tandem intermolecular hydroalkoxylation/ claisen rearrangement

An efficient yttrium-catalyzed tandem intermolecular hydroalkoxylation/Claisen rearrangement has been developed, providing various γ,δ-unsaturated amides in generally good to excellent yields. Importantly, high Z/E selectivity and diastereoselectivity were achieved. Other notable features of this method include widespread availability of the substrates, compatibility with a broad range of functional groups, and mild reaction conditions.

Synthesis of α,β-Unsaturated N-Sulfonyl Imides through Zinc-Catalyzed Intermolecular Oxidation of N-Sulfonyl Ynamides

A novel zinc-catalyzed intermolecular oxidation of N-sulfonyl ynamides has been developed. A variety of functionalized α,β-unsaturated N-sulfonyl imides are readily accessed by utilizing this approach, thus providing a viable alternative to synthetically

Zeo-click synthesis: Copper-zeolite-catalyzed synthesis of ynamides

Copper(I)-zeolites, especially copper(I)- ultra stable Y zeolite (USY), are very efficient heterogeneous catalysts for the coupling of functionalized 1-bromoalkynes and various nitrogen derivatives. Under these conditions, sulfonylated alkyl- or aryl- ACHTUNGTRENUNGamines and various N-heterocycles, such as oxazolidinones or indoles, could be efficiently transformed into the corresponding N-alkynyl derivatives. However, imidazoles gave addition products rather than coupling products. The reaction conditions proved compatible with a variety of functional and protecting groups. Such zeolitic catalysts can be recycled and reused at least five times without significant deactivation. Low catalyst loading could be used (4 mol%) and as low as 0.8 mol% of this heterogeneous copper catalyst still gave good conversion and yields.

Regio- and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation

A facile approach to (E)-α-haloenamide moieties from ynamides using bromo- or iodotrimethylsilane is described. The simple protocol enables a regio- and stereospecific hydrohalogenation of the triple bond in gram-scale and provides a general entry for synthesis of novel enamide analogues.

Enantioselective ficini reaction: Ruthenium/PNNP-catalyzed [2+2] cycloaddition of ynamides with cyclic enones

(Chemical Equation Presented) Chiral cyclobuteneamides made easy: Double chloride abstraction from the ruthenium/PNNP complex 1 in the presence of unsaturated β-keto esters 2 gives the dicationic adducts [Ru(2)(PNNP)] 2+ (3) that catalyze the [2+2] cycloaddition of a variety of ynamides 4 to produce cyclo-buteneamides 5 with high yield and enantioselectivity (see scheme).

Radical additions of arenethiols to ynamides for the selective synthesis of N-[(Z)-2-(Arylsulfanyl)-1-alkenyl]amides

A variety of ynamides undergo highly regio- and stereoselective radical addition of arenethiols with the aid of trie- thylborane as a radical initiator. The products, N-[-2-arylsulfanyl-1 -alkenyl]amides, can be reduced with triethyl- silane in trifluoroa

Iron-catalyzed amidation of alkynyl bromides: A facile route for the preparation of ynamides

(Chemical Equation Presented) A facile route to obtain ynamides in high yields was described. The products were achieved through the iron-catalyzed C-N coupling reaction of amides with alkynyl bromides in the presence of 20 mol % of N,N′-dimethylethane-1,2-diamine (DMEDA).