94026-72-9

Upstream product

• 4783-67-9 N,N-dimethyl-3-(pyridin-2-yloxy)aniline 
• 28557-00-8 phenylzinc chloride 
• 98-80-6 phenylboronic acid 
• 6848-13-1 3-chloro-N,N-dimethylaniline 
• 108-88-3 toluene 
• 15799-79-8 3-methoxy-N,N-dimethylaniline 
• 1589-82-8 phenylmagnesium bromide 
• 100-44-7 benzyl chloride 

Relevant academic research and scientific papers

Nickel-Catalyzed Cross-Coupling of Aryl 2-Pyridyl Ethers with Organozinc Reagents: Removal of the Directing Group via Cleavage of the Carbon-Oxygen Bonds

Reaction of aryl 2-pyridyl ethers with arylzinc reagents under catalysis of NiCl2(PCy3)2 affords aryl-aryl cross-coupling products via selective cleavage of CAr-OPy bonds. The reaction features a wide substrate range and good compatibility of functional groups. β-H-free alkylzinc reagents are also applicable as the nucleophiles in the transformation, whereas β-H-containing alkylzinc reagents lead to a mixture of cross-coupling and hydrogenation products.

Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides

Suzuki cross-coupling of benzylic and unactivated aliphatic fluorides with aryl- and alkenylboronic acids has been achieved via mechanistically distinct Pd and Ni catalyzed pathways that outperform competing protodeboronation, β-hydride elimination, and h

Ni(NIXANTPHOS)-Catalyzed Mono-Arylation of Toluenes with Aryl Chlorides and Bromides

A nickel-catalyzed cross-coupling of toluene derivatives with both aryl bromides and chlorides using a NIXANTPHOS-ligated nickel(II) complex has been developed. The key factor to success is proposed to be the catalyst activation of toluene by a cation-π complex, enabling methyl arenes (pKa ≈ 43) to be deprotonated with the relatively mild base NaN(SiMe3)2. This method facilitates access to a variety of sterically and electronically diverse hetero- and nonheteroaryl-containing 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.

Nickel-Catalyzed Cross-Coupling of Anisoles with Alkyl Grignard Reagents via C-O Bond Cleavage

Nickel-catalyzed cross-coupling of methoxyarenes with alkyl Grignard reagents, which involves the cleavage of the C(aryl)-OMe bond, has been developed. The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand allows the introduction of a variety of alkyl groups, including Me, Me3SiCH2, ArCH2, adamantyl, and cyclopropyl. The method can also be used for the alkylative elaboration of complex molecules bearing a C(aryl)-OMe bond.