25940-64-1Relevant academic research and scientific papers
Nickel-Catalyzed Synthesis of N-(Hetero)aryl Carbamates from Cyanate Salts and Phenols Activated with Cyanuric Chloride
Dindarloo Inaloo, Iman,Esmaeilpour, Mohsen,Majnooni, Sahar,Reza Oveisi, Ali
, p. 5486 - 5491 (2020/09/04)
A simple and efficient domino reaction has been designed and employed for the one-pot synthesis of N-(hetero)aryl carbamates through the reaction between alcohols and in-situ produced (hetero)aryl isocyanates in the presence of a nickel catalyst. The phenolic C?O bond was activated via the reaction of phenol with cyanuric chloride (2,4,6-trichloro-1,3,5-triazine (TCT)) as an inexpensive and readily available reagent. This strategy provides practical access to N-(hetero)aryl carbamates in good yields with high functional groups compatibility.
Nickel-catalysed C–O bond reduction of 2,4,6-triaryloxy-1,3,5-triazines in 2-methyltetrahydrofuran
Wang, Yaoyao,Shen, Jun,Chen, Qun,Wang, Liang,He, Mingyang
, p. 409 - 412 (2018/10/02)
A nickel-catalysed reduction of phenol derivatives activated by 2,4,6-trichloro-1,3,5-triazine (TCT) in ecofriendly 2-methyltetrahydrofuran (2-MeTHF) is described. The phenol-TCT derivatives were readily prepared using grinding method in short time without further purification. This catalytic system allowed the facile C–O cleavage of phenol-TCT derivatives under mild reaction conditions with high efficiency and good functional group tolerance. Gram-scale reaction was also achieved. Particularly, sequential functionalization of phenol-TCT derivatives followed by C–O bond reduction could also be realized, affording the high value-added products in moderate to good yields.
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
supporting information, p. 2753 - 2756 (2018/05/22)
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.
Nickel-catalyzed cyanation of phenol derivatives activated by 2,4,6-trichloro-1,3,5-triazine
Wang, Liang,Wang, Yaoyao,Shen, Jun,Chen, Qun,He, Ming-Yang
supporting information, p. 4816 - 4820 (2018/07/13)
A nickel-catalyzed cyanation of phenol derivatives activated by 2,4,6-trichloro-1,3,5-triazine (TCT) using aminoacetonitrile as the cyanating agent is described. This catalytic system delivered the desired products in moderate to good yields with good substrate compatibility. The readily available starting materials, cost-effective nickel catalyst and metal-free cyanating agent are the major features of the present method.
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 deoxygenation and reductive homocoupling of phenols via C-O activation using TCT reagent
Iranpoor, Nasser,Panahi, Farhad
supporting information, p. 214 - 217 (2015/01/30)
A new method for C-O bond activation of phenolic compounds has been achieved using 2,4,6-trichloro-1,3,5-triazine to utilize in one-pot Ni-catalyzed deoxygenation and reductive homocoupling reactions. With this simple method, phenolic compounds were converted to their corresponding arenes or biaryl compounds under mild conditions. The introduced methodology has a broad scope and demonstrates good functional group compatibility.
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.
In vitro cytotoxic activities of 2-alkyl-4,6-diheteroalkyl-1,3,5-triazines: New molecules in anticancer research
Menicagli, Rita,Samaritani, Simona,Signore, Giovanni,Vaglini, Francesca,Dalla Via, Lisa
, p. 4649 - 4652 (2007/10/03)
The cytotoxic activities of new 2-alkyl-4,6-dihetero-(N,O)alkyl-1,3,5- triazines toward selected tumor cell lines have been evaluated, and for the first time, the potential of 2-alkyl-4,6-dialkoxy-1,3,5-triazines has been shown.
Microwave assisted synthesis of triaryl cyanurates
Sagar,Patil,Bandgar
, p. 1719 - 1723 (2007/10/03)
Rapid synthesis of triaryl cyanurates(2,4,6-triaryloxy-1,3,5-triazine) was carried out by reacting cyanuric chloride with the sodium salt of hydroxyaryl compounds in water using focused microwaves. Environmentally friendly procedure and isolation of pure products in excellent yields are important features of this method.
