705265-30-1

Upstream product

• 100-42-5 styrene 
• 2142-69-0 2-bromophenyl methyl ketone 
• 70916-14-2 triethyl-(2-oxo-2-phenylethyl)ammonium bromide 
• 70-11-1 α-bromoacetophenone 
• 1034330-25-0 C₁₃H₁₇BO₂ 
• 2142-70-3 2-iodoacetophenone 

Downstream Products

• 1413394-31-6 (Z)-2-chloro-1-[2-(2-phenylethenyl)phenyl]ethanon 
• 1413394-42-9 (Z)-2-chloro-1-[2-(2-phenylethenyl)phenyl]ethanon 

Relevant academic research and scientific papers

Ruthenium(0)-Catalyzed Cross-Coupling of Anilines with Organoboranes by Selective Carbon-Nitrogen Cleavage

Selective activation of neutral carbon-nitrogen bonds is of great synthetic importance, because amines are among the most prevalent motifs across organic and bioactive molecules. Herein, we report the Ru(0)-catalyzed selective cleavage of neutral C(aryl)-N bonds in generic aniline derivatives enabled by a combination of Ru3(CO)12 and an imino auxiliary. These mild conditions provide a direct route to high-value biaryl ketones and biaryl aldehydes after facile in situ hydrolysis. A broad range of organoboranes and anilines can be coupled with high C-N cleavage selectivity. Most crucially, the reaction achieves exquisite selectivity for activation of C(aryl)-N bonds in the presence of typically more kinetically favorable C(aryl)-H bonds. The method provides a strategy for the construction of functionalized terphenyls by exploiting orthogonal properties of the Ru(0) catalyst system and traceless nucleophilic properties of anilines.

Achieving Site Selectivity in Metal-Catalyzed Electron-Rich Carbene Transfer Reactions from N-Tosylhydrazones

Catalyst control of the site-selectivity of electron-rich alkyl, aryl disubstituted carbenes generated in situ from o-alkenyl-substituted N-tosylhydrazones was achieved in this study. Exposure of these substrates to copper iodide triggered the formation of α-alkoxy 2H-naphthalenones. This investigation established that changing the catalyst to a rhodium(II) carboxylate turned off cyclization and migration of the electron-rich metal carbene with the β-carboxylate and turned on allylic C-H bond functionalization to diastereoselectively afford 1H-indenes. Examination of the scope of this reaction revealed that ethereal, aminomethylene, and unactivated 2° C-H bonds could be functionalized.

Immobilized palladium nanoparticles on potassium zirconium phosphate as an efficient recoverable heterogeneous catalyst for a clean Heck reaction in flow

Palladium nanoparticles on layered potassium α-zirconium phosphate (PdNP/α-ZrPK) with high palladium loading (10.6 wt%) have been prepared and used as catalyst in low amount (0.1 mol% of Pd) in the Heck reaction of methyl acrylate and styrene with a series of aryl iodides in CH3CN/H2O azeotrope as a green medium. The procedure has been optimized under flow conditions obtaining an extremely low waste production (E-factor) and allowing to isolate the final product with very low residual palladium content without any purification step.

Rhodium-catalyzed C-H activation of phenacyl ammonium salts assisted by an oxidizing C-N bond: A combination of experimental and theoretical studies

Rh(III)-catalyzed C-H activation assisted by an oxidizing directing group has evolved to a mild and redox-economic strategy for the construction of heterocycles. Despite the success, these coupling systems are currently limited to cleavage of an oxidizing

6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl]: A new ligand for palladium-catalyzed Mizoroki-Heck coupling

A novel and conveniently prepared diphosphine ligand 6H-Dibenzo[d,f-[1,3] diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl] (DADPP) combined with [Pd(C3H5)Cl]2 affords an efficient catalytic system for Mizoroki-Heck cross-coupling of aryl halides with alkenes. The system could give the yield of 95% for 4-chloronitrobenzene with 0.05 mol.% [Pd(C 3H5)Cl]2. For the bromide-substituted substrates, the highest turnover number (TON) is up to 96,000,000.

6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl]: A new ligand for palladium-catalyzed Mizoroki-Heck coupling

A novel and conveniently prepared diphosphine ligand 6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl] (DADPP) combined with [Pd(C3H5)Cl]2affords an efficient catalytic system for Mizoroki-Heck cross-coupling of aryl halides with alkenes. The system could give the yield of 95% for 4-chloronitrobenzene with 0.05 mol.% [Pd(C3H5)Cl]2. For the bromide-substituted substrates, the highest turnover number (TON) is up to 96,000,000.

Highly regioselective Heck-Mizoroki reaction catalyzed by Pd/phosphine ligand in DMSO/[bmim][BF4] under microwave irradiation

This work established that highly regioselective Heck-Mizoroki arylation of olefins can be accomplished with aryl halides using Pd2(dba) 3 (dba = dibenzylideneacetone) with phosphine ligand L [L = methyl 4,6-O-benzylidene-3-deoxy-3-(diphenylphosphino)-α-D-altropyranoside] as catalyst in DMSO/[bmim][BF4] under microwave irradiation. In addition, the use of microwave irradiation greatly reduces the reaction time (from hours to minutes), allows low catalyst loading (0.01 mol%) and affords nearly quantitative product yields. ARKAT-USA, Inc.