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Upstream product

• 766-47-2 1-ethynyl-2-methylbenzene 
• 611-15-4 1-methyl-2-vinyl-benzene 
• 90399-62-5 1-(1,2-dibromo-ethyl)-2-methyl-benzene 

Downstream Products

• 1295522-05-2 1,8-dimethyl-3,4-diphenylisoquinoline 
• 1449389-85-8 1-benzyl-2-phenyl-4-(o-tolyl)-1H-imidazole 
• 88089-30-9 3-(o-tolyl)-2H-azirine 
• 16216-13-0 2-phenyl-1-o-tolylethanone 
• 529-19-1 2-Methylbenzonitrile 
• 5330-79-0 4-(2-methylphenyl)-1,3-thiazol-2-amine 

Relevant academic research and scientific papers

Lewis Acid Catalyzed Diastereoselective Cycloaddition Reactions of Donor-Acceptor Cyclopropanes and Vinyl Azides: Synthesis of Functionalized Azidocyclopentane and Tetrahydropyridine Derivatives

Lewis acid catalyzed [3 + 2]-cycloaddition reaction of donor-acceptor cyclopropanes with vinyl azides has been developed to obtain diastereomerically enriched azidocyclopentane derivatives. In addition, thermal chemoselective ring expansion of azidocyclopentanes to tetrahydropyridine derivatives and further diastereospecific reduction to a substituted piperidine derivative, with an excellent yield, was also achieved.

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

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.

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.).

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.

Visible-Light-Induced Regioselective C(sp3)-H Acyloxylation of Aryl-2 H-azirines with (Diacetoxy)iodobenzene

A visible-light-promoted regioselective coupling of C(sp3)-H of aryl-2H-azirine and (diacetoxy)iodobenzene has been reported. Rose Bengal as an organophotoredox catalyst has been used in this reaction. The reaction proceeds under aerobic condition at room temperature. A variety of aryl-2H-azirines gives the corresponding acyloxylated azirines under this reaction conditions. The reaction goes through a radical pathway. The protocol is also applicable on gram-scale synthesis.

Switchable reactivity between vinyl azides and terminal alkyne by nano copper catalysis

A novel nano copper-catalyzed substrate-dependent chemodivergent transformation of vinyl azides with a terminal alkyne is disclosed. 2,5-Disubstituted pyrroles were selectively obtained in high yield with aryl alkynes and aliphatic alkynes, whereas 2,3,4-trisubstituted pyrroles were formed with silylated alkynes. This switchable method provides a controllable and facile access to both multisubstituted pyrrole scaffolds with high efficiency, excellent regioselectivity, and good functional group compatibility.

Rhodium-Catalyzed Double Isocyanide Insertion via a Vinylcarbodiimide Intermediate for the Synthesis of 2H-Pyrrol-2-imines

2 H -Pyrrol-2-imine is an important structural motif exhibiting in biologically active compounds and natural products. An efficient rhodium-catalyzed one-pot reaction of one vinyl azide with sequentially with two different isocyanides is reported, which offers an alternative facile access to 3-amino-5-aryl-2 H -pyrrol-2-imines bearing various substitution on the nitrogens in good yields. An unstable vinylcarbodiimide is the key intermediate in this cascade reaction.

Transformation of Alkynes into α- Or β-Difluorinated Alkyl Azides by an Efficient One-Pot Two-Step Procedure

Reported herein an unprecedented 1,2-azide migratory hydroazidation and subsequent gem-difluorination of alkynes accessing β-difluorinated alkyl azides. Importantly, functional group controlled 1,2-azide or 1,2-aryl migration was observed in the case of a