1237776-30-5

Upstream product

• 100-42-5 styrene 
• 1632-83-3 1-Methylbenzimidazole 
• 59871-40-8 2-benzyl-1-methyl-1H-benzo[d]imidazole 
• 74-88-4 methyl iodide 
• 3319-28-6 N-methyl-2-(α-hydroxyethyl)benzimidazole 
• 71-43-2 benzene 

Downstream Products

• 1222-07-7 1-(1-methyl-1H-benzo[d]imidazol-2-yl)-1-phenylethanol 

Relevant academic research and scientific papers

Cu-Catalyzed Regioselective C-H Alkylation of Benzimidazoles with Aromatic Alkenes

Herein we report a novel Cu-catalyzed regioselective C2-H alkylation of benzimidazoles with aromatic alkenes. The reaction features exclusive regioselectivity and broad substrate scope in the intermolecular alkylation of benzimidazoles with terminal and i

N-Heterocyclic Carbene Ligand-Controlled Regioselectivity for Nickel-Catalyzed Hydroarylation of Vinylarenes with Benzothiazoles

A facile regioselective switch for nickel-catalyzed hydroarylation of vinylarenes with benzothiazoles has been developed, which relies on the simple structural variation of novel Ni(II) complexes of the type Ni(NHC)[P(OR)3]Br2. Using magnesium turnings as the reductant, Ni(IMes)[P(OEt)3]Br2 afforded branched products, while Ni(IPr?OMe)[P(OEt)3]Br2 created steric demand to afford linear products. This work also provides a rare example of the rational design of heteroleptic Ni(II) complexes that display the required air stability, reactivity, and regioselectivity via synergism between NHC and phosphite ligands.

Reactions of 2-carbonyl- And 2-hydroxy(or methoxy)alkylsubstituted benzimidazoles with arenes in the superacid CF3SO3H. NMR and DFT studies of dicationic electrophilic species

Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkylbenzimidazoles with arenes in the Br?nsted superacid TfOH resulted in the formation of the corresponding Friedel-Crafts reaction products, 2-diarylmethyl and 2-arylmethyl-substituted benzimidazoles, in yields up to 90%. The reaction intermediates, protonated species derived from starting benzimidazoles in TfOH, were thoroughly studied by means of NMR and DFT calculations and plausible reaction mechanisms are discussed.

Iron-Catalyzed Aerobic Oxidation of (Alkyl)(aryl)azinylmethanes

An iron-catalyzed aerobic oxidation of (alkyl)(aryl)azinylmethanes has been developed leading to tertiary alcohols in moderate to good yields. Hock rearrangement was identified as a major side reaction leading to a complex mixture of undesired products. Addition of thiourea sometimes allows inhibiting this side reaction and steers the reaction towards the desired products.

Mechanistic study of a switch in the regioselectivity of hydroheteroarylation of styrene catalyzed by bimetallic Ni-Al through C-H activation

We previously reported a highly efficient protocol for bimetallic Ni-Al-catalyzed hydroheteroarylation of styrene with benzimidazole based on C-H bond activation. We have now delineated the mechanism of this process, providing a rationale for an observed switch in regioselectivity in the presence of the Lewis acid, AlMe3. The present mechanistic study gives insights for the rational development of catalysts that exhibit required linear/branched selectivity. Lewis acid switches regioselectivity: The mechanism underpinning a highly efficient protocol for bimetallic Ni-Al-catalyzed hydroheteroarylation of styrene with benzimidazole based on C-H bond activation has been unraveled (see scheme). The study gives insights that can be used for the rational development of catalysts that give the required linear/branched selectivity.

The regioselective switch for amino-NHC mediated C-H activation of benzimidazole via Ni-Al synergistic catalysis

We have disclosed a new mode of a chemically regioselective switch for C-H bond functionalization of benzimidazole derivatives via a cooperative effect invoked by Ni-Al bimetallic catalysis to create a steric requirement for obtaining the linear product of styrene insertion. Yet, excluding the AlMe 3 cocatalyst switches the reaction toward branch selectivity.

Nickel-catalyzed hydroheteroarylation of vinylarenes

(Figure Presented) In the nickel of time: A nickel/carbene catalyst effects the hydroheteroarylation of vinylarenes to give 1,1-diarylethanes that contain various heteroaryl moieties with excellent regioselectivity. EWC = electron-withdrawing group.