73013-48-6Relevant articles and documents
Nickel-Catalyzed Mono-Selective α-Arylation of Acetone with Aryl Chlorides and Phenol Derivatives
Amgoune, Abderrahmane,Derhamine, Sary Abou,Krachko, Tetiana,Monteiro, Nuno,Pilet, Guillaume,Schranck, Johannes,Tlili, Anis
supporting information, p. 18948 - 18953 (2020/09/01)
The challenging nickel-catalyzed mono-α-arylation of acetone with aryl chlorides, pivalates, and carbamates has been achieved for the first time. A nickel/Josiphos-based catalytic system is shown to feature unique catalytic behavior, allowing the highly selective formation of the desired mono-α-arylated acetone. The developed methodology was applied to a variety of (hetero)aryl chlorides including biologically relevant derivatives. The methodology has been extended to the unprecedented coupling of acetone with phenol derivatives. Mechanistic studies allowed the isolation and characterization of key Ni0 and NiII catalytic intermediates. The Josiphos ligand is shown to play a key role in the stabilization of NiII intermediates to allow a Ni0/NiII catalytic pathway. Mechanistic understanding was then leveraged to improve the protocol using an air-stable NiII pre-catalyst.
Domino Synthesis of Benzo-Fused β,γ-Unsaturated Ketones from Alkenylboronic Acids and N-Tosylhydrazone-Tethered Benzonitriles
Plaza, Manuel,Paraja, Miguel,Florentino, Lucía,Valdés, Carlos
supporting information, p. 632 - 635 (2019/02/07)
The transition-metal-free domino reaction between alkenylboronic acids and N-tosylhydrazones from o-(2-oxoalkyl)- and o-(3-oxoalkyl)benzonitriles leads to β, γ-unsaturated indanones and tetralones featuring an α-"all-carbon" quaternary center. The employment of derivatives of α-substituted cyclopentanones and cyclohexanones led to the stereoselective preparation of β, γ-unsaturated tetrahydrocyclopenta[a]inden-8(1H)-ones, hexahydrofluorenones, and hexahydroanthracenones as cis-fused single stereoisomers. A domino sequence involving diazo compound formation/reductive alkenylation/1,3-borotropic rearrangement/intramolecular bora-aza-ene reaction is proposed to justify the formation of the products as well as the stereoselectivity.
C-H arylation reactions through aniline activation catalysed by a PANI-g-C3N4-TiO2 composite under visible light in aqueous medium
Wang, Liang,Shen, Jun,Yang, Sen,Liu, Wenjie,Chen, Qun,He, Mingyang
supporting information, p. 1290 - 1296 (2018/03/26)
A PANI (polyaniline)-g-C3N4-TiO2 composite was prepared and found to be efficient for radical C-H arylation reactions. The arylation process involved coupling of in situ generated aryl diazonium salts from aniline with heteroarenes, enol acetates or benzoquinones under visible light in aqueous medium or pure water. A broad range of substrates survived the reaction conditions to provide the desired products in moderate to good yields. Scale-up (10 mmol) synthesis was also achieved. This semiconductor photocatalyst showed good photocatalytic performance and stability. Recycle studies showed that this composite could be readily recovered and a slight decrease in the catalytic activity was observed after ten consecutive runs.