25649-41-6Relevant articles and documents
Nickel-Catalyzed Deoxycyanation of Activated Phenols via Cyanurate Intermediates with Zn(CN)2: A Route to Aryl Nitriles
Heravi, Majid M.,Panahi, Farhad,Iranpoor, Nasser
, p. 2753 - 2756 (2018)
A novel, and efficient nickel-catalyzed deoxycyanation of phenolic compounds using relatively nontoxic Zn(CN)2 as the cyanide source was developed. The reaction of C-O bond activated phenolic compounds by 2,4,6-trichloro-1,3,5-triazine with Zn(CN)2 in the presence of a nickel precatalyst afforded the aromatic nitriles in good to excellent yields.
A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multiphasic Continuous Flow
Zhao, Yuhan,King, Georgina,Kwan, Maria H.T.,Blacker, A. John
supporting information, p. 2012 - 2018 (2017/02/10)
A low-energy, high-selectivity approach to the catalytic hydrodeoxygenation of phenols is reported using batch or continuous flow methods to react 3 equiv of phenol with cyanuric chloride then hydrogenolyzing the triarylcyanurate intermediate to give 3 equiv of deoxo aromatic. The use of cyanuric chloride compares favorably with existing activation methods, showing improved scalability, atom efficiency, and economics. The scope of both the activation and hydrogenolysis stages are explored using lignin-related phenols. Initial development has identified that continuous stir tank reactors (CSTRs) enable a multiphasic process for converting guaiacol to anisole and at steady state overcome the catalyst deactivation issues observed in batch, seemingly caused by the cyanurate byproduct. Green chemistry aspects and the potential for industrial adoption are discussed.
Nickel-catalyzed one-pot synthesis of biaryls from phenols and arylboronic acids via C-O activation using TCT reagent
Iranpoor, Nasser,Panahi, Farhad,Jamedi, Fereshteh
, p. 6 - 10 (2015/03/05)
In this study, the direct Nickel-catalyzed Suzuki-Miyaura coupling reaction of phenols and arylboronic acids via C-O bond activation using 2,4,6-trichloro-1,3,5-triazine (TCT) is described. Initially, phenols were reacted with TCT to give the corresponding 2,4,6-triaryloxy-1,3,5-triazine (TAT) products. Subsequently, arylboronic acid, base and Ni-catalyst were added to the generated aryl C-O electrophile to obtain the final biaryl product. This study represents a simple and direct method for the synthesis of biaryls from phenolic compounds using sub-stoichiometric amounts of TCT as a cheap and readily available C-O activating reagent.
