Sustainable Synthesis of Substituted 1,3,5-Triazines by [ONO]-Pincer-Supported Nickel(II) Complexes via an Acceptorless Dehydrogenative Coupling Strategy
Anandaraj Pennamuthiriyan1, Ramesh Rengan1, Jan Grzegorz Malecki2
1Centre for Organometallic Chemistry, School of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamilnadu, India.
Abstract:
A facile, cost-effective, and sustainable synthesis of substituted triazines from primary alcohols by newly synthesized nickel pincer-type complexes (1-3) has been described. Herein, we report the synthesis of a set of three well-defined Ni(II) O^N^O pincer-type complexes, structurally characterized by analytical, spectral, and X-ray diffraction techniques. Further, the nickel complexes are explored as efficient catalysts (4 mol %) for the construction of 2,4,6-substituted 1,3,5-triazines from readily available alcohols via an acceptorless dehydrogenative coupling (ADC) strategy. A wide range of substituted triazine derivatives (33 examples) has been synthesized from the coupling of alcohols and benzamidine/guanidine hydrochloride with a maximum isolated yield of 92% under mild conditions, with eco-friendly H2O and H2 gas as the only byproducts. A plausible mechanism has been proposed based on a sequence of control experiments. Interestingly, the short synthesis of the antiulcer drug irsogladine and the large-scale synthesis of 2,4-diphenyl-6-(p-tolyl)-1,3,5-triazine highlight the convenience of the current methodology.
More Related Videos
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Related Concept Videos
Diazonium Group Substitution: –OH and –H
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of Nitriles
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
