67541-85-9

Upstream product

• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 577-16-2 2-Methylacetophenone 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1271055-11-8 1-methyl-2-(4-phenylbuta-2,3-dien-2-yl)benzene 
• 1269206-78-1 2-(1-o-tolylethyl)benzo[d]oxazole 
• 1275593-37-7 2-(1-(o-tolyl)vinyl)phenol 
• 1638139-67-9 1-benzyl-3-methyl-2-(1-(o-tolyl)vinyl)benzene 
• 1301683-21-5 ethyl 2-methyl-5-(2-tolyl)furan-3-carboxylate 
• 1198806-90-4 1-benzyl-4-(2'-methylphenyl)-1H-1,2,3-triazole 
• 1063605-68-4 2,2'-(buta-1,3-diene-2,3-diyl)bis(methylbenzene) 
• 1160942-78-8 C₂₁H₂₁OP 
• 75193-12-3 [(CH₃C₆H₄CCH₂)Co(N₄C₄₄H₂₈)] 

Relevant academic research and scientific papers

Copper-Catalyzed Reductive N-Alkylation of Amides with N-Tosylhydrazones Derived from Ketones

A CuI-catalyzed reductive coupling of ketone-derived N-tosylhydrazones with amides is presented. Under the optimized conditions, an array of N-tosylhydrazones derived from aryl–alkyl and diaryl ketones could couple effectively with a wide variety of (hete

Copper(I)/Bpy-Catalyzed C-2-H Benzylation of Quinazolin-4(3H)-ones with N-Tosylhydrazones

A general and efficient copper-catalyzed C–H benzylation reaction of quinazolin-4(3H)-ones with N-tosylhydrazones is reported. The formation of new C(sp3)–C(sp2) bonds through cross-coupling occurs at the electron-poor C-2 position of quinazolin-4(3H)-one and represents an exceedingly practical method to afford 2-benzylated quinazolin-4(3H)-ones in moderate to good yields under mild reaction conditions. A possible reaction mechanism for this transformation was proposed. This catalytic transformation has the potential to be an important synthetic application for the late-stage functionalization of advanced synthetic intermediates.

I2-Promoted [4 + 2] cycloaddition of: In situ generated azoalkenes with enaminones: Facile and efficient synthesis of 1,4-dihydropyridazines and pyridazines

A facile and efficient strategy for the synthesis of 1,4-dihydropyridazines and pyridazines through I2-promoted [4 + 2] cycloaddition of in situ generated azoalkenes with enaminones has been developed. The switch in selectivity is attributed to the judici

Synthesis of Multi-substituted Dihydropyrazoles by Copper-Mediated [4+1] Cycloaddition Reaction of N-Sulfonylhydrazones and Sulfoxonium Ylides

A general and expeditious approach for the copper mediated synthesis of multi-functionalized dihydropyrazoles from N-sulfonylhydrazones and sulfoxonium ylides has been achieved under aerobic oxidative conditions. The formal [4+1] cycloaddition reaction ex

Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles

An efficient and practical C–N bond formation methodology for the synthesis of N-alkylated (benzo)thiazoles was developed, via the copper-catalyzed one-pot two-step reactions of 2-amino(benzo)thiazoles and aldehydes (ketones) with tosylhydrazide. This cross-coupling reaction proceeded smoothly and tolerated a broad range of functional groups (46 examples). A variety of functionalized N-alkylated (benzo)thiazoles were obtained in moderate to high yields. Notably, gram-scale synthesis of fanetizole (anti-inflammatory drug) was also realized through this protocol.

Asymmetric Copper-Catalyzed C(sp)-H Bond Insertion of Carbenoids Derived from N-Tosylhydrazones

A chiral copper(I)-phosphoramidite complex efficiently catalyzed the asymmetric insertion of the carbenoids derived from N-tosyl hydrazones into alkyne C-H bonds to give the corresponding chiral alkynylated products in up to 77% yield and with up to 74% e

Cooperative Iodide Pd(0)-Catalysed Coupling of Alkoxyallenes and N-Tosylhydrazones: A Selective Synthesis of Conjugated and Skipped Dienes

Palladium(0)-catalysed hydro-alkylation or -alkenylation of alkoxyallenes with N-tosylhydrazones gives direct access to conjugated and skipped 1-alkoxydienes with high efficiency and excellent functional-group compatibility. The reaction is proposed to in

Rhodium-Catalyzed B-H Bond Insertion Reactions of Unstabilized Diazo Compounds Generated in Situ from Tosylhydrazones

Although transition-metal-catalyzed B-H bond insertion of carbenes into stable borane adducts has emerged as a promising method for organoborane synthesis, all the diazo compounds used to date as carbene precursors have had an electron-withdrawing group to stabilize them. Herein, we report a protocol for rhodium-catalyzed B-H bond insertion reactions of unstabilized diazo compounds generated in situ from tosylhydrazones. In addition, by using chiral dirhodium catalysts, we also achieved an asymmetric version of the reaction with good to excellent enantioselectivities (up to 98:2 e.r.). This is the first enantioselective heteroatom-hydrogen bond insertion reaction to use unstabilized diazo compounds as carbene precursors. The protocol exhibited good functional group tolerance and could be carried out on a gram scale. It also enabled one-pot transformation of a carbonyl group to a boryl group enantioselectively. The B-H bond insertion products could be easily transformed into chiral alcohols and other widely used organoboron reagents with enantiomeric fidelity.

Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source

A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.

Copper catalysed alkylation of heteroaryl chloride via migratory insertion of carbenes

Cross-coupling reaction involving Cu catalysed carbene migratory insertion with N-tosylhydrazones as the reaction partner with various substituted cyanuric chloride were studied, which has been recognized as a new type of cross-coupling reaction. Cu-carbe