52374-25-1

Upstream product

• 149552-43-2 [N-(nosyl)imino]phenyliodinane 
• 108-88-3 toluene 
• 32337-46-5 Phenyl p-nitrobenzenesulphonate 
• 100-46-9 benzylamine 
• 30362-87-9 p-Nitrophenyl p-nitrobenzenesulphonate 
• 321578-69-2 4-tolyl 4-nitrobenzenesulfonate 
• 128886-84-0 p-Chlorophenyl p-nitrobenzenesulphonate 
• 156840-00-5 2,4-dinitrophenyl 4-nitrobenzenesulfonate 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 100-51-6 benzyl alcohol 
• 108-30-5 succinic acid anhydride 
• 100-39-0 benzyl bromide 
• 63160-16-7 4-nitro-N-(phenylmethylene)benzenesulfonamide 

Downstream Products

• 329354-10-1 N-benzyl-4-nitro-N-trimethylsilanylethynyl-benzenesulfonamide 

Relevant academic research and scientific papers

Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides

A cobalt-catalyzed 1,4-aryl migration/disulfonylation cascade applied to α-bromo N-sulfonyl amides was developed. The reaction was highly chemoselective, allowing the preparation of α-aryl amides possessing a variety of functional groups. The method was used as the key step to synthesize an alkaloid, (±)-deoxyeseroline. Mechanistic investigations suggest a radical process.

Ynamides as Three-Atom Components in Cycloadditions: An Unexplored Chemical Reaction Space

While 1,3-dipolar cycloadditions have appeared to be a fertile area for research, as attested by the numerous synthetic transformations and resulting applications that have been developed during the past 60 years, the use of neutral three-Atom components (TACs) in (3+2) cycloadditions remains comparatively sparse. Neutral TACs, however, have great synthetic potential given that their reaction with a πsystem can produce zwitterionic cycloadducts that may be manipulated for further chemistry. We report herein that ynamides, a class of carbon πsystems that has seen wide interest over the last two decades, can be used as neutral TACs in thermally induced intramolecular (3+2) cycloaddition reactions with alkynes to yield a variety of functionalized pyrroles. The transformation is proposed to occur in a stepwise manner via the intermediacy of a pyrrolium ylide, from which the electron-withdrawing group on the nitrogen atom undergoes an intramolecular 1,2-shift to produce the neutral pyrrole. This work demonstrates a yet unexplored facet of ynamide reactivity with great potential in heterocyclic chemistry.

Arylation and alkenylation of activated alkyl halides using sulfonamides

A variety of quaternary aryl amino acid derivatives can be synthesised using tandem SN2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C-N and C-Caryl bond under simple conditions with no requirement for organometallics or transition metal catalysts. The reaction is also successful for alkenyl sulfonamides, producing sterically congested quaternary alkene amino acid derivatives.

A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives

A novel transition-metal-free cascade reaction to synthesize 4-quinolone derivatives has been demonstrated. Michael addition and Truce-Smiles rearrangement are included in this protocol, providing a broad scope of 4-quinolones in moderate-to-excellent yields. This work serves as an example of the use of sulfonamides through Truce-Smiles rearrangement to build heterocyclic compounds under mild conditions.

Nitrene Insertion into Aromatic and Benzylic C?H Bonds Catalyzed by Copper Complexes of Fluorinated Bis- and Tris(pyrazolyl)borates

Fluorinated bis- and tris(pyrazolyl)boratocopper complexes catalyze the nitrene insertion to C?H bonds of aromatic hydrocarbons efficiently producing amination products in good to excellent yields at room temperature. Imidoiodanes, PhI=NTs (Ts=p-toluenesulfonyl) and PhI=NNs (Ns=p-nitrophenylsulfonyl) serve as the nitrene source. The bis(pyrazolyl)borate catalyst [H2B(3,5-(CF3)2Pz)2]Cu(NCMe) with PhI=NNs produced the arene C?H functionalized product of mesitylene in 87 % yield with only trace amounts of benzylic C?H insertion. The use of [H2B(3,5-(CF3)2-4-(NO2)Pz)2]Cu(NCMe) that has an even weakly donating pyrazolate generated the arene C?H insertion product exclusively. The tris(pyrazolyl)borate complex [HB(3,5-(CF3)2Pz)3]Cu(NCMe), in contrast, generated the benzylic amination product from mesitylene and PhI=NNs in 82 % yield with only very minor amounts of arene C?H functionalization. DFT calculations suggest that Cu-nitrene moiety generated from [HB(3,5-(CF3)2Pz)3]Cu(NCMe) and PhI=NNs activates the benzylic C?H bond of mesitylene via a hydrogen atom abstraction (HAA) followed by a radical rebound (RR) pathway, whereas the functionalization of sp2 C?H bonds of mesitylene by [H2B(3,5-(CF3)2Pz)2]Cu(NNs) ensues possibly via a nitrene addition to the arene core.

Reductions of Imines Using Zirconocene Chloride Hydride

Herein, we describe the fast, chemoselective, and clean reduction of imines with zirconocene chloride hydride. The reaction works well on aromatic and enolizable aliphatic aldimines, as well as ketimines. A range of N-protecting groups and various functio

Metal-free synthesis of activated ynesulfonamides and tertiary enesulfonamides

An operationally simple synthesis of activated ynesulfonamides and enesulfonamides is described. Ynesulfonamides can be obtained through reaction of sulfonylamides with activated bromoalkynes and Triton B in a short time at room temperature. Likewise, terminal alkynes react with sulfonylamides to provide enesulfonamides. Z/E enesulfonamides can be transformed exclusively into E enesulfonamides.

A Micellar Catalysis Strategy for Amidation of Alkynyl Bromides: Synthesis of Ynamides in Water

Copper-catalyzed amidation of alkynyl bromides can be carried out in water for the first time, which is made possible by a micellar catalysis strategy using rosin-based surfactant APGS-550-M. The surfactant can be easily prepared from natural abundant biomass, resin acids. Studies as to substrate scope and reaction aqueous medium recycling showcase the ease and sustainability of this technology.

Method for catalytic synthesis of N-benzyl benzene sulfonamide compounds by boric acid/oxalic acid catalytic system under microwave radiation

The invention discloses a method for catalytic synthesis of N-benzyl benzene sulfonamide compounds by a boric acid/oxalic acid catalytic system under microwave radiation. The method includes: adoptingbenzyl alcohol and derivatives thereof and benzene sulfonamide derivatives as raw materials, adopting the boric acid/oxalic acid system as a catalyst, and adopting fluorobenzene as a solvent; performing reaction in a microwave reactor under certain temperature and power conditions, performing vacuum concentration after reaction for a period of time, and subjecting a product to column chromatographic purification to realize efficient catalytic preparation of the N-benzyl benzene sulfonamide compounds. Compared with the prior art, the method has advantages of evidently higher reaction speed than that of conventional heating, mild reaction conditions, simplicity in operation, high yield, safety, low cost and environmental friendliness.

Highly Selective Syn Addition of 1,3-Diones to Internal Ynamides Catalyzed by Zinc Iodide

1,3-Diones are already established as nucleophiles to perform additions to ynamides; the highly selective hydroalkoxylation of internal ynamides is now described. Several catalytic systems have been compared to perform this transformation, including transition-metal-based catalysts and Lewis acids. ZnI2 was found to be both very active and highly selective providing only E adducts through a syn addition. Investigation of the scope and limitations showed that this catalyst was compatible with various functional groups. In addition to seventeen examples of ynamide hydroalkoxylation, one example of ynamide hydroarylation is reported.