Recent advances in nickel-catalyzed C–C and C–N bond formation via HA and ADC reactions

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(19), P. 4213 - 4227

Published: Jan. 1, 2021

In this review article, recent advances in nickel-catalyzed hydrogen auto-transfer (HA) and acceptorless dehydrogenative coupling (ADC) reactions for the construction of C–C C–N bonds have been discussed.

Language: Английский

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Nickel(II)–N^ΛN^ΛO Pincer Type Complex-Catalyzed N-alkylation of Amines with Alcohols via the Hydrogen Autotransfer Reaction

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(11), P. 7125 - 7135

Published: May 8, 2020

A highly sustainable catalytic protocol for the coupling of alcohols and amines selective monoalkylated using Ni(II)–NΛNΛO pincer type complexes through borrowing hydrogen methodology is described. An array Ni(II) catalysts (1–3) was synthesized characterized by various spectral analytical methods. Furthermore, distorted square planar geometry (1 2) substantiated with single crystal X-ray diffraction study. The inexpensive nickel-based displays a broad substrate scope N-alkylation aromatic heteroaromatic diverse range primary excellent yields up to 97%. present approach environmentally benign, which liberates water as sole byproduct. short synthesis drug intermediates such mepyramine chloropyramine illustrates utility protocol.

Language: Английский

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Ruthenium pincer complex catalyzed efficient synthesis of quinoline, 2-styrylquinoline and quinazoline derivatives via acceptorless dehydrogenative coupling reactions

Catalysis Science & Technology, Journal Year: 2022, Volume and Issue: 12(18), P. 5695 - 5702

Published: Jan. 1, 2022

The synthesis of N-heterocycles has been considered an emerging area chemical research due to their extensive utilization in pharmaceuticals, materials science, and natural product synthesis.

Language: Английский

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Olefins from alcohols via catalytic acceptorless dehydrogenation coupling reactions

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(8), P. 2064 - 2089

Published: Jan. 1, 2024

Recent advances in efficient catalytic routes to olefins from alcohols (A2O) are highlighted.

Language: Английский

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Design and Syntheses of Palladium Complexes of NNN/CNN Pincer Ligands: Catalyst for Cross Dehydrogenative Coupling Reaction of Heteroarenes

Organometallics, Journal Year: 2020, Volume and Issue: 39(2), P. 324 - 333

Published: Jan. 13, 2020

This report describes simple syntheses of a new class palladium(II) pincer complexes having NNN and CNN coordination modes. The were fully characterized with the help 1H 13C{1H} NMR, HRMS, IR spectroscopy. structure bonding modes further authenticated single-crystal X-ray diffraction. Thermally robust moisture-/air-insensitive palladium C1–C4 have been used as catalysts for cross dehydrogenative coupling (CDC) reactions two heteroarenes found to be very efficient. catalyst was successful in activating C–H bond variety heteroarenes, including benzimidazole, imidazole, benzothiazole, imidazopyridine, thiophene, furan, only 1.0 mol % catalyst, achieving excellent yields coupled products. showed tolerance toward functional groups such CHO, COMe, COOMe, COOEt, CONHPh, Me, CN, Br, Cl. Further, is reusable up four reaction cycles minor loss its efficiency. mechanism CDC investigated through control experiments, it has suggested that acetate analogue ligand (C5) active catalyst.

Language: Английский

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C(sp³)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds

European Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 2020(15), P. 2155 - 2179

Published: March 18, 2020

Quinolines and their derivatives have always been promising leads for drug discovery, material applications designing new catalysts. In the past decade, C(sp 3 )‐H functionalization of 2‐methyl azaarenes, particularly quinolines, has become one highly facile synthetic routes generation chemical libraries quinolines. this minireview, we showcase endeavors on

Language: Английский

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Pincer-Nickel Catalyzed Selective Guerbet-Type Reactions

Organometallics, Journal Year: 2021, Volume and Issue: 40(16), P. 2870 - 2880

Published: Aug. 5, 2021

We report here the synthesis and characterization of a series NNN pincer-nickel complexes type (R2NNN)NiCl2(CH3CN) (R = iPr, tBu, Cy, Ph, p-F-C6H4) based on bis(imino)pyridine ligands. In solution, these are found to be equilibrium mixtures containing one two pincer ligands, respectively. While crystal structure former was reported by us recently for R we latter in this study p-F-C6H4. The considered pincer-Ni have been successfully employed accomplish catalytic β-alkylation several secondary alcohols with variety benzyl at 140 °C high yields unprecedented turnovers. A maximum 92% yield β-alkylated product 18 400 TON obtained reaction alcohol 1-(4-(trifluoromethyl)phenyl)ethane-1-ol presence 0.005 mol % (Ph2NNN)NiCl2(CH3CN) 5 NaOtBu after 24 h. exhibits zero-order dependence rate catalyst concentration first-order base, alcohol, 1-phenyl ethanol which points base-mediated aldol condensation as rate-determining step. Most intermediates involved catalysis identified HRMS. To best our knowledge, is first catalyzed and, hitherto, such turnovers not homogeneous molecular nickel-based catalyst.

Language: Английский

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A strategic approach for Csp³–H functionalization of 9H-fluorene: an acceptorless dehydrogenation and borrowing hydrogen approach

Catalysis Science & Technology, Journal Year: 2023, Volume and Issue: 13(3), P. 611 - 617

Published: Jan. 1, 2023

Herein, we described the selective synthesis of both alkylated and alkenylated fluorenes using a single SNS ligand derived nickel complex.

Language: Английский

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Cobalt-catalyzed alkylation of methyl-substituted N-heteroarenes with primary alcohols: direct access to functionalized N-heteroaromatics

Chemical Communications, Journal Year: 2019, Volume and Issue: 56(2), P. 249 - 252

Published: Nov. 27, 2019

Phosphine free, air and moisture stable Co(NNN) complex catalyzed alkylation of various methyl-substituted N-heteroarenes with alcohols is reported. Following the borrowing hydrogen methodology, a variety can be functionalized efficiently. To understand mechanism this reaction kinetic control experiments were carried out.

Language: Английский

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Copper-Catalyzed 8-Aminoquinoline-Directed Oxidative C–H/N–H Coupling for N-Arylation of Sulfoximines

Organic Letters, Journal Year: 2020, Volume and Issue: 22(7), P. 2606 - 2610

Published: March 17, 2020

A copper-catalyzed cross-dehydrogenative C–H/N–H coupling has been devised to access a series of N-arylated sulfoximines in high yield from 8-aminoquinoline-derived benzamides and sulfoximines. The reaction is scalable, mechanistic studies favor the involvement an organometallic pathway, where C–H bond cleavage presumed be kinetically relevant step. utility sulfoximine-coupled was displayed through nickel-catalyzed acceptorless dehydrogenative olefination benzyl alcohols.

Language: Английский

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