19946-98-6

Upstream product

• 100-42-5 styrene 
• 98-86-2 acetophenone 
• 14428-98-9 (E)-1-phenyl-N-(1-phenylethylidene)methanamine 
• 2743-00-2 (E)-4-methoxy-N-(1-phenylethylidene)benzenamine 
• 622-24-2 2-phenylethyl chloride 
• 103-63-9 1-phenyl-2-bromoethane 
• 2142-69-0 2-bromophenyl methyl ketone 

Relevant academic research and scientific papers

Chelation-assisted RhI-catalyzed ortho-alkylation of aromatic ketimines or ketones with olefins

Described herein is the RhI-catalyzed ortho-alkylation of aromatic ketimines or ketones with olefins. This method showed high reactivity and selectivity to monoalkylation for a variety of olefins including 1-alkenes with an allylic proton, a,w-

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.

Highly linear selective cobalt-catalyzed addition of aryl imines to styrenes: Reversing intrinsic regioselectivity by ligand elaboration

Highly linear selective, imine-directed hydroarylation of styrene has been achieved with cobalt-based catalytic systems featuring bis(2,4-dimethoxyphenyl)(phenyl)phosphine and either 2-methoxypyridine or DBU as a ligand and a Lewis base additive, respectively, thus affording a variety of 1,2-diarylethanes (bibenzyls) in good yields under mild reaction conditions. The triarylphosphine controls the regioselectivity, while the Lewis base significantly accelerates the reaction. Ligand screening and deuterium-labeling studies provide implications about the roles of the ligand and the Lewis base in the crucial C-C reductive elimination step.

Cobalt-catalyzed chelation-assisted alkylation of arenes with primary and secondary alkyl halides

Cobalt-N-heterocyclic carbene catalytic systems have been developed for chelation-assisted ortho-alkylation of aromatic compounds with alkyl halides. Aryl imines can be selectively monoalkylated at room temperature by various primary or secondary alkyl chlorides or bromides. The catalytic system can also be applied to 2-arylpyridine derivatives, which in the absence of steric hindrance are amenable to dialkylation by an excess of the alkyl halide. Mechanistic experiments, including reactions of stereochemical probes and radical clocks, indicate that the reaction involves single-electron transfer from the cobalt center to the alkyl halide to form the corresponding alkyl radical, which has a finite lifetime before it undergoes C-C bond formation. Georg Thieme Verlag Stuttgart, New York.

Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides

We report here cobalt-N-heterocyclic carbene catalytic systems for the ortho alkylation of aromatic imines with alkyl chlorides and bromides, which allows the introduction of a variety of primary and secondary alkyl groups at room temperature. The stereochemical outcomes of the reaction of secondary alkyl halides suggest that the present reaction involves single-electron transfer from a cobalt species to the alkyl halide to generate the corresponding alkyl radical. A cycloalkylated product obtained by this method can be transformed into unique spirocycles through manipulation of the directing and cycloalkyl groups.

Cobalt-catalyzed branched-selective addition of aromatic ketimines to styrenes under room-temperature conditions

An improved cobalt-based catalytic system has been developed for the branched-selective addition of aromatic ketimines to styrenes. With an appropriate combination of triarylphosphine and the Grignard reagent, the reaction takes place smoothly at room temperature to afford 1,1-diarylethane derivatives with high regioselectivity.

Regioselectivity-switchable hydroarylation of styrenes

Cobalt-phosphine and cobalt-carbene catalysts have been developed for the hydroarylation of styrenes via chelationassisted C-H bond activation, to afford branched and linear addition products, respectively, in a highly regioselective fashion. Deuterium-la

Cobalt-phenanthroline catalysts for the ortho alkylation of aromatic imines under mild reaction conditions

Mild mannered: Cobalt catalysts complexed with phenanthroline-type ligands and activated with Grignard reagents serve as inexpensive and effective catalysts for the ortho alkylation of aromatic imines with a variety of olefins (see scheme). The new catalytic systems feature remarkably mild reaction conditions for C-H bond activation and functionalization. Copyright

Anti-Markovnikov hydroarylation of styrenes catalyzed by an in situ generated ruthenium complex

An efficient and practical catalytic system for the anti-Markovnikov ruthenium-catalyzed hydroarylation of styrenes with acetophenone, allowing a straightforward access to bibenzyl backbones, is described for the first time: this process, involving regios

Ruthenium-catalysed ortho alkylation of hydroxyacetophenones; the functionalisation of ring C aromatic diterpenoids

Ortho C-H bond coupling of some 2-alkoxyacetophenones with olefins catalysed by ruthenium complexes results in a high yield of the ortho alkylated product, providing that a suitable protecting group is employed. No such protection was required for a para-alkoxy group; an activating effect was also observed. Bicyclic and tricyclic analogues react similarly.