89108-49-6

Upstream product

• 766-97-2 4-n-methylphenylacetylene 
• 33458-08-1 1-(1,2-dibromoethyl)-4-methylbenzene 
• 1352574-56-1 1-(1-azido-2-bromoethyl)-4-methylbenzene 
• 1092459-96-5 1-(1-azido-2-iodoethyl)-4-methylbenzene 
• 622-97-9 1-ethenyl-4-methylbenzene 

Downstream Products

• 21399-23-5 2,5-di(4-methylphenyl)-1H-pyrrole 
• 122-00-9 para-methylacetophenone 
• 1073483-63-2 ethyl 2-methyl-5-p-tolyl-1H-pyrrole-3-carboxylate 
• 1073483-85-8 1-(2-methyl-5-p-tolyl-1H-pyrrol-3-yl)ethanone 
• 128994-27-4 (S)-γ-(4-methylphenyl)-γ-butyrolactone 
• 65964-60-5 2-para-tolylimidazo[1,2-a]pyridine 
• 65964-61-6 7-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine 
• 61001-04-5 2-(4-methylphenyl)imidazo[2,1-a]isoquinoline 
• 73475-24-8 2-(p-methylphenyl)aziridine 
• 65241-92-1 5-(4-methylphenyl)-2,3-diphenyl-1H-pyrrole 
• 1619224-90-6 1,6-dimethyl-3-(p-tolyl)isoquinoline 

Relevant academic research and scientific papers

Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates

A metal-free visible light photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates in moderate to high yields is described. The reaction proceeds in ethanol and uses eosin Y as a readily available photocatalyst in combination with nitrobenzene as an electron shuttle. Taking into account the number of steps involved (generation of the sulfonyl radical, its addition to the double bond, elimination of molecular nitrogen with formation of an iminyl radical, followed by its reduction and protonation) as well as the number of redox-active reaction partners involved, the selectivity of the process is quite impressive.

Electrosynthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates mediated by NH4I

A wide range of N-unsubstituted enaminosulfones were obtained via electrochemical sulfonylation of vinyl azides with sulfonyl radicals generated from sodium sulfinates. The discovery of N-unsubstituted enaminosulfones synthesis is based on a unique ability of the azido group to eliminate the N2 molecule. The process is performed under constant current conditions in an experimentally convenient undivided electrochemical cell equipped with a graphite anode and a stainless steel cathode applying NH4I both as the redox catalyst and the supporting electrolyte.

A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach

The reported flow-batch approach enables the easy preparation of 2H-azirines and their stereoselective transformation into highly functionalized NH-aziridines, starting from vinyl azides and organolithium compounds. The protocol has been developed using c

Electrochemical Oxidative Cross-Coupling between Vinyl Azides and Thiophenols: Synthesis ofgem-Bisarylthio Enamines

An electrochemical radical strategy involving alkene substrates provides a powerful approach for alkene functionalization. Herein, we described the first electrochemical synthesis ofgem-bisarylthio enamines from vinyl azides and thiophenols through the C-

Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides

Sulfonylated N-unsubstituted enamines were synthesized through a chain of chemical and electrochemical transformations via sulfonylation of vinyl azides. The disclosing of the N-unsubstituted enamines synthesis was based on a unique property of the azido group, which is its ability to eliminate the N2 molecule. Furthermore, a formal paradox is observed: A double bond reacts and a double bond is retained. Electrosynthesis proceeded in an undivided cell equipped with a graphite anode and a stainless steel cathode; NH4I was used as a supporting electrolyte.

Electrochemical Synthesis of O-Phthalimide Oximes from α-Azido Styrenes via Radical Sequence: Generation, Addition and Recombination of Imide-N-Oxyl and Iminyl Radicals with C?O/N?O Bonds Formation

Electrochemically induced radical-initiated reaction of vinyl azides with N-hydroxyphthalimide resulting O-phthalimide oximes with challenging for organic chemistry N?O-N fragment has been discovered. The developed approach introduces in synthesis electrochemically generated O-centered imide-N-oxyl radicals as the coupling components. Sequential formation of C?O and N?O bonds was achieved via generation and selective addition of imide-N-oxyl radicals, followed by recombination with iminyl radicals. A wide range of O-phthalimide oximes was obtained with the yields up to 84percent. (Figure presented.).

Synthesis of Isoquinoline Derivatives via Palladium-Catalyzed C?H/C?N Bond Activation of N-Acyl Hydrazones with α-Substituted Vinyl Azides

A palladium-catalyzed cyclization of N-acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α-substituted vinyl azide serves as an internal nitrogen source. Also, C?H bond activation and C?N bond cleavage have been realized using hydrazone as directing group. (Figure presented.).

Access to Cycloalkeno[ c]-Fused Pyridines via Pd-Catalyzed C(sp2)-H Activation and Cyclization of N-Acetyl Hydrazones of Acylcycloalkenes with Vinyl Azides

A novel Pd(II)-catalyzed vinylic C-H activation and cyclization has been developed, reacting a series of small, medium, and large N-acetyl hydrazones of acylcycloalkenes with vinyl azides to access diverse cycloalkeno[c]-fused pyridine scaffolds. This protocol provides progress in C(sp2)-H bond activation of medium to large cycloalkenes, and the target products can be obtained in a specific regioselectivity with good functional group tolerance and a broad substrate scope.

Indium(iii) catalyzed reactions of vinyl azides and indoles

Indium trichloride catalyzes the reaction of vinyl azides with unfunctionalized indoles to give vinyl indoles. This is the first example of displacement of the azide group by a carbon nucleophile while preserving the vinyl function. The protocol employs very mild reaction conditions and offers excellent yields of diverse 3-vinyl indoles. It is amenable to gram scale. Access to a library of 3,3′-bis(indolyl)methanes through condensation of vinyl azides with 2 equiv of an indole is demonstrated.

Cerium(IV) ammonium nitrate promoted synthesis of O-phthalimide oximes from vinyl azides and N-hydroxyphthalimide

O-Phthalimide oximes with an N–O–N fragment were synthesized in high yields via the reaction of vinyl azides with phthalimide-N-oxyl radicals derived from N-hydroxyphthalimide under the action of cerium(IV) ammonium nitrate. The disclosed process is based on the radical transformation of vinyl azides with the elimination of nitrogen and the formation of iminyl N-radicals. The developed approach exploited the dual reactivity of imide-N-oxyl radicals. They act as O-components for oxidative C–O coupling with vinyl azides and participate in subsequent formation of the N–O bond via their recombination with intermediate iminyl radicals.