Herein, we report an efficient nickel-catalyzed direct cyclization of amines with alcohols for the synthesis of various nitrogen containing heterocycles. These processes employ the sustainable "borrowing hydrogen" strategy and have many advantages, such as earth-abundant metal catalysts, easily available starting materials, wide synthetic versatility and harmless waste emission.
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Nickel-Catalyzed Chemodivergent Coupling of Alcohols: Efficient Routes to Access α,α-Disubstituted Ketones and α-Substituted Chalcones.
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Organometallic Synthesis and Catalysis Lab, Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune, 411 008, India.
Chemodivergent (de)hydrogenative coupling of primary and secondary alcohols is achieved utilizing an inexpensive nickel catalyst, (6-OH-bpy)NiCl . This protocol demonstrates the synthesis of branched carbonyl compounds, α,α-disubstituted ketones, and α-substituted chalcones via borrowing hydrogen strategy and acceptorless dehydrogenative coupling, respectively. A wide range of aryl-based secondary alcohols are coupled with various primary alcohols in this tandem dehydrogenation/hydrogenation reaction.
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J Org Chem
January 2023
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India.
The "borrowing hydrogen" (BH) approach for the N-alkylation of phenylenediamines using alcohols as coupling partners is highly challenging due to the selectivity issue of the generated products. Furthermore, the development of base-metal systems that can potentially substitute precious metals with competitive activity is a major challenge in BH catalysis. We present herein an efficient protocol for the N,N'-di-alkylation of aromatic diamines using an in situ-generated Ni-NHC complex from NiCl and the ligand , which gave access to a wide range of N,N'-di-alkylated orthophenylene diamines (rather than the generally observed benzimidazole derivatives), - and -phenylene diamines along with 2,6-diamino pyridine derivatives in good to excellent yields.
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College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan, 250014, P. R. China.
We report here our findings on the diverse reaction results of sulfones and alcohols. In the presence of NiCl/P(-Bu) and under a N atmosphere, α--alkylation of sulfones with alcohols occurs through a borrowing-hydrogen mechanism; when the reaction was carried out in the open air without nickel, the product was not the predicted α,β-unsaturated sulfone, but the β-alkenyl sulfone, which is a useful building block in organic synthesis.
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Org Biomol Chem
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Ege University, Department of Chemistry, 35100 Bornova, Izmir, Turkey.
Nickel(II)-salen or nickel(II)-salphen catalyzed α-alkylation of ketones and nitriles with primary alcohols is reported. Various α-alkylated ketones and nitriles were obtained in high yields through a borrowing hydrogen strategy by using 1-3 mol% of nickel catalyst and a catalytic amount of NaOH (5-10 mol%) under aerobic conditions.
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September 2021
Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Botanic Garden, Howrah 711103, India.
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