90564-68-4

Upstream product

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

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 
• 5330-79-0 4-(2-methylphenyl)-1,3-thiazol-2-amine 
• 529-19-1 2-Methylbenzonitrile 
• 16216-13-0 2-phenyl-1-o-tolylethanone 
• 1616735-16-0 1-methyl-3-(o-tolyl)isoquinoline 

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.

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.

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.

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