72046-76-5

Upstream product

• 55343-50-5 9-(4-methoxy-benzyl)-9-bora-bicyclo[3.3.1]nonane 
• 21702-84-1 2,4-dibromoanisole 
• 25445-34-5 1-methoxy-2,4-bis(chloromethyl)benzene 
• 21130-91-6 triethoxy(4-methoxyphenyl)silane 
• 24318-41-0 p-methoxybenzyl benzoate 
• 100-66-3 methoxybenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 83020-58-0 2,4-bis(bromomethyl)-1-methoxybenzene 
• 553-82-2 1,3-dichloro-4-methoxybenzene 
• 824-94-2 p-methoxybenzyl chloride 
• 104-82-5 4-Methylbenzyl chloride 
• 105-13-5 4-Methoxybenzyl alcohol 
• 38769-92-5 4-methoxybenzylmagnesium chloride 

Relevant academic research and scientific papers

Heteroleptic Ni(II) Complexes Bearing a Bulky Yet Flexible IBiox-6 Ligand: Improved Selectivity in Cross-Electrophile Coupling of Benzyl Chlorides with Aryl Chlorides/Fluorides

A bisoxazoline-derived NHC known as IBiox-6 reacted smoothly with Ni[P(OEt)3]2Br2 and Ni(PPh3)2Br2 to give the respective heteroleptic Ni(II) complexes Ni(IBiox-6)[P(OEt)3]Br2 (1) and Ni(IBiox-6)(PPh3)Br2 (2) in yields of 60% and 71%. Their crystal structures were characterized to reveal a rare cis disposition of the IBiox-6 ligand to the phosphite ligand in 1, while 2 possessed the more common trans configuration. Both complexes catalyzed the cross-electrophile coupling of benzyl chlorides with aryl chlorides and fluorides in the presence of Mg turnings at 50 °C via a "real one-pot"procedure, featuring no requirement for temperature variation or portionwise addition of any coupling partner. In particular, complex 1 showed a better balance between the catalytic activity and selectivity. The scope of the procedure catalyzed by 1 and Mg turnings was investigated, providing a highly selective, simple, and practical approach to the synthesis of diarylmethanes with high steric hindrance and various functional groups, including oligo-diarylmethane with asymmetric structures.

Ligand-Facilitated Reductive Coupling of Benzyl Chlorides with Aryl Chlorides Catalyzed by Well-Defined Heteroleptic Ni (II)-NHC Complexes

Novel heteroleptic Ni (II) complexes bearing a highly hindered yet flexible IPr* ligand, Ni (IPr*)(PPh3)Br2 (1) and Ni (IPr*)(PCy3)Br2 (2) (IPr* = 1,3-bis(2,6-bis (diphenylmethyl)-4-methylphenyl)imidazol-2-ylidene), were easily prepared in 78percent and 89percent yield, respectively. Both were characterized by elemental analysis and NMR spectroscopy, and 1 was subjected to X-ray crystallography. Compared with 2 and its analogue bearing a less sterically demanding IPr ligand (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), complex 1 exhibited superior catalytic activity in the magnesium-mediated reductive coupling of benzyl chlorides with aryl chlorides, featuring outstanding tolerance of both coupling partners with steric demand. This study discloses a ligand-facilitated reductive coupling of benzyl chlorides with aryl chlorides, which provides a new and practical synthetic tool for the synthesis of diarylmethanes.

Nickel-Catalyzed Reductive Cross-Coupling of Benzyl Chlorides with Aryl Chlorides/Fluorides: A One-Pot Synthesis of Diarylmethanes

The first nickel-catalyzed, magnesium-mediated reductive cross-coupling between benzyl chlorides and aryl chlorides or fluorides is reported. A variety of diarylmethanes can be prepared in good to excellent yields in a one-pot manner using easy-to-access mixed PPh3/NHC Ni(II) complexes of Ni(PPh3)(NHC)Br2 (NHC = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, IPr, 1a; 1,3-di-tert-butylimidazol-2-ylidene, ItBu, 1b) as catalyst precursors. Activation of polychloroarenes or chemoselective cross-coupling based on the difference in catalytic activity between 1a and 1b is used to construct oligo-diarylmethane motifs.

Direct C(sp2)-C(sp3) cross-coupling of diaryl zinc reagents with benzylic, primary, secondary, and tertiary alkyl halides

The direct C(sp2)-C(sp3) cross-coupling of diaryl zinc reagents with benzylic, primary, secondary, and tertiary alkyl halides proceeded in the absence of coordinating ethereal solvents at ambient temperature without the addition of a catalyst. The C(sp2)-C(sp3) cross-coupling showed excellent functional-group tolerance, and products were isolated in high yields, generally without the requirement for purification by chromatography. This process represents an expedient, operationally simple method for the construction of new C(sp2)-C(sp3) bonds. Zinc and you'll miss it. Direct C(sp2)-C(sp3) cross-coupling of diaryl zinc reagents with alkyl halides proceeded rapidly at ambient temperature without a coordinating ethereal solvent or an added catalyst (see scheme). This versatile, operationally simple approach to C(sp2)-C(sp3) bond formation enables the expedient construction of a diverse array of carbon-based structural motifs.

Proton-exchanged montmorillonite-mediated reactions of methoxybenzyl esters and ethers

Proton-exchanged montmorillonite (H-mont) was found to be an eco-friendly and cost-effective catalyst for the generation of O-methylated quinone methides (QM) from the corresponding p or o-methoxybenzyl esters and ethers. Nucleophilic trapping of the O-methylated QM with arenes, alcohols, 1,3-dicarbonyl compounds, silyl enol ethers, and allylsilanes has been carried out, respectively, leading to eco-friendly benzylation reactions. Using this protocol, H-mont-mediated deprotection of PMB-protected esters and ethers have been realized for the first time. This work would pave the way for further exploration in O-alkylated QM that are of chemical and biological significance.

Palladium nanoparticle catalyzed hiyama coupling reaction of benzyl halides

An efficient Hiyama coupling reaction between benzylic halide and aryltrialkoxysilane using Pd nanoparticles has been developed. This procedure accommodates various functional groups to yield a diverse range of diarylmethanes which are ubiquitous units of natural products and pharmaceuticals.

Catalytic dehydrative etherification and chlorination of benzyl alcohols in ionic liquids

Dibenzyl ethers and benzyl chloride can be obtained in moderate to excellent yields through Pd-catalysed reactions in hydrophobic ionic liquids using microwave or conventional heating. The Royal Society of Chemistry 2009.

Palladium-catalyzed cross-coupling of B-Benzyl-9-borabicyclo[3.3.1]nonane to furnish methylene-linked biaryls

(Chemical Equation Presented) Benzylboranes are noticeably uncommon partners within Suzuki-Miyaura coupling reactions. B-Benzyl-9-BBN was successfully coupled to a range of aryl/heteroaryl bromides, chlorides, and triflates to give pharmacologically important methylene-linked biaryl structures. Activated, deactivated, and sterically hindered substrates were successfully coupled in high yield using Pd(PPh3)4 or Pd(OAc)2 with SPhos as the catalyst system.