1292358-68-9

Upstream product

• 941-55-9 4-toluenesulfonyl azide 
• 772-38-3 4-tert-Butylphenylacetylene 

Downstream Products

• 1638238-72-8 (E)-4-(4-(tert-butyl)phenyl)-2-styryl-1-tosyl-2,3-dihydro-1H-pyrrole 
• 1638238-60-4 6-(4-(tert-butyl)phenyl)-2-phenyl-1-tosyl-2,5-dihydro-1H-azepine 
• 1638238-92-2 4,6-bis(4-(tert-butyl)phenyl)-1-tosyl-2,5-dihydro-1H-azepine 
• 35222-80-1 p-tert-butyl-NH-1,2,3-triazole 
• 1613045-70-7 (Z)-N-(3-(4-(tert-butyl)phenyl)-1-(dimethylamino)-3-oxo-1-phenylprop-1-en-2-yl)-4-methylbenzenesulfonamide 
• 1613045-71-8 C₂₈H₃₂N₂O₃S 
• 1598463-48-9 N-(2-(4-(tert-butyl)phenyl)-2-(4-(diethylamino)phenyl)vinyl)-4-methylbenzenesulfonamide 
• 1598463-49-0 N-(2-(4-(tert-butyl)phenyl)-2-(4-(diethylamino)phenyl)vinyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Cycloaddition of: N -sulfonyl and N -sulfamoyl azides with alkynes in aqueous media for the selective synthesis of 1,2,3-triazoles

The cycloaddition of N-sulfonyl and N-sulfamoyl azides with terminal alkynes generally produces amide derivatives via ketenimine intermediates. We herein delineate a Cu(i) catalyzed method using a prolinamide ligand that selectively generates N-sulfonyl a

Rhodium(II)-Catalyzed [4+3] Cyclization of Triazoles with Indole Derivatives and Its Application in the Total Synthesis of (±)-Aurantioclavine

An efficient rhodium(II)-catalyzed [4+3] cyclization reaction of 1-sulfonyl-1,2-3-triazoles and indoles was developed. Azepino[5,4,3- cd]indoles, which are widely distributed in ergot alkaloids with various biological activities, could be obtained in good

Copper(I)-N-Heterocyclic Carbene Complexes as Efficient Catalysts for the Synthesis of 1,4-Disubstituted 1,2,3-Sulfonyltriazoles in Air

Bis-NHC and mixed NHC/PR3 copper(I) complexes (NHC = N-heterocyclic carbene) were found to be efficient catalysts enabling the azide-alkyne cycloaddition reaction leading to the formation of 1,2,3-sulfonyltriazoles under Click conditions. The mechanism of this transformation was probed and decoordination of the NHC ligand (even in the NHC/PR3 mixed ligand systems) during the catalytic transformation was observed.

Synthesis of β-amino-α,β-unsaturated ketone derivatives via sequential rhodium-catalyzed sulfur ylide formation/rearrangement

In the presence of a Rh(II) catalyst and β-(methylthio)-α,β-unsaturated ketones, 1-sulfonyl-1,2,3-triazoles can be converted into functionalized β-amino-α,β-unsaturated ketones via formation of α-imino rhodium carbene/sulfur ylide and subsequent rearrangement. The products decompose to useful 2-methylthiopyrrole derivatives conveniently in high yield.

Rhodium-Catalyzed Synthesis of 2,5-Epoxybenzo[f][1,4]oxazepines by Tandem Reaction of 1-Sulfonyl-1,2,3-triazoles and Salicylaldehydes

Readily available 1-sulfonyl-1,2,3-triazoles were converted into α-imino carbenes in the presence of catalytic amounts of rhodium(II) salts. The carbenes underwent a tandem reaction with salicylaldehydes to provide a series of functionalized 2,5-epoxybenzo[f][1,4]oxazepines in high yields. A novel protocol for the synthesis of 2,5-epoxybenzo[f][1,4]oxazepines is developed. The complicated ring system can be constructed from readily available N-sulfonyl-1,2,3-triazoles and salicylaldehyde derivatives in a one-pot procedure. Many valuable functional groups are well tolerated in this transformation. [Rh2(piv)4] = dirhodium(II) tetrapivalate.

One-Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides

A general and efficient one-pot aminoethylation of substituted indoles/pyrroles was accomplished for the synthesis of various tryptamine derivatives employing a combination of alkynes and sulfonyl azides as readily accessible aminoethylating agents. The reaction features a successful integration of copper-catalyzed alkyne and azide cycloaddition to N-sulfonyl-1,2,3-triazole, rhodium-catalyzed selective insertion of α-iminocarbenes onto the C3-H bond of indoles, and reduction of the resultant enamides to tryptamine derivatives employing either NaCNBH3 or palladium catalyst, in one-pot. The reaction also showed excellent functional-group tolerance and allowed the synthesis of various substituted tryptamines in good to excellent yield. This transformation constitutes a one-pot formal regioselective functionalization of terminal alkynes. Utility of the synthesized tryptamine was further demonstrated in the synthesis of dihydro-β-carboline and tryptoline.

Rhodium(II)-Catalyzed Formal [3 + 2] Cycloaddition of N-Sulfonyl-1,2,3-triazoles with Isoxazoles: Entry to Polysubstituted 3-Aminopyrroles

A novel rhodium(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with isoxazoles has been achieved that provides an efficient method for the synthesis of polysubstituted 3-aminopyrrole derivatives. An operationally simple one-pot synthesis of the titled compounds from terminal alkynes, tosyl azide, and isoxazoles was also developed. The presented reaction affords an illustrative example of employing 1,2,3-triazoles as the [2C]-component in relevant cycloaddition reactions.

Cu2O acting as a robust catalyst in CuAAC reactions: Water is the required medium

Cu2O as the catalyst in water was found to be quite robust for the azide-alkyne cycloaddition (AAC) reaction, which was verified by a wide variety of applicable azides and alkynes. Water was proved to play an essential role because of a significant rate acceleration compared with reactions using organic solvents and conducted under neat conditions. The high catalytic performance of Cu2O/H2O system was further argued by decreasing the catalyst loading to ppm levels. The Royal Society of Chemistry.