Nickel-Catalyzed Alkylation of Oxindoles with Secondary Alcohols

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7162 - 7171

Published: May 10, 2023

Herein, we have demonstrated a simple nickel-catalyzed C-3-selective alkylation of 2-oxindoles using wide variety secondary alkyl alcohols. As special highlight, functionalization the cholesterol derivative was reported. Control experiments, initial mechanistic studies, and deuterium-labeling experiments were performed for process.

Language: Английский

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Phosphine‐Free NNN‐Manganese(II) Catalyzed C‐alkylation of Methyl N‐Heteroarenes via Borrowing Hydrogen

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(7), P. 1531 - 1537

Published: Jan. 31, 2024

Abstract Mn(II)‐catalyzed alkylations of methyl N ‐heteroarenes was reported via borrowing hydrogen strategy with alcohols as the alkylating reagent. The developed geometry‐constrained benzimidazole‐iminopyridyl ligand played a key role in promoting transformation and stablizing metal center. A wide range (aromatic, heteroaromatic aliphatic) ‐Heteroarenes could be able to apply current catalytic system, TON up 7400.

Language: Английский

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Quinoline-derived NNP-manganese complex catalyzed α-alkylation of ketones with primary alcohols

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(25), P. 5112 - 5116

Published: Jan. 1, 2024

An air-stable quinoline-derived NNP ligand chelated Mn catalyst was developed for the efficient α-alkylation of ketones with primary alcohols

Language: Английский

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Copper-Catalyzed Borrowing Hydrogen Reaction for α-Alkylation of Amides with Alcohols

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9654 - 9660

Published: June 20, 2024

We report the first example of copper-catalyzed α-alkylation acetamides with alcohols via a borrowing hydrogen strategy. Catalyzed by in situ-generated copper particles, and various substituted benzyl or alkyl were transformed into functionalized amides good yields excellent selectivity. Compared previous work, this process is simple using commercially available Cu(OAc)2 as precatalyst, without an additional ligand metal complex, easier. Mechanistic studies revealed that aldehyde α,β-unsaturated intermediates reaction also disclosed role alcohol dehydrogenation C═C bond hydrogenation.

Language: Английский

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Iron-Catalyzed sp³ C–H Alkylation of Fluorene with Primary and Secondary Alcohols: A Borrowing Hydrogen Approach

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16223 - 16241

Published: Aug. 23, 2024

The utilization of earth-abundant, cheap, and nontoxic transition metals in important catalytic transformations is essential for sustainable development, iron has gained significant attention as the most abundant metal. A mixture FeCl2 (3 mol %), phenanthroline (6 KOtBu (0.4 eqivalent) was used an effective catalyst sp3 C–H alkylation fluorene using alcohol a nonhazardous alkylating partner, eco-friendly water formed only byproduct. substrate scope includes wide range substituted fluorenes benzyl alcohols. reaction equally with challenging secondary alcohols unactivated aliphatic Selective mono-C9-alkylation yielded corresponding products good isolated yields. Various postfunctionalizations C-9 alkylated were performed to establish practical utility this alkylation. Control experiments suggested homogeneous path involving borrowing hydrogen mechanism formation subsequent reduction 9-alkylidene intermediate.

Language: Английский

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Hydrosilylative reduction of secondary amides to amines catalyzed by geometry-constrained NNN-cobalt complexes

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(12), P. 5603 - 5610

Published: Jan. 1, 2023

An efficient Co-catalyzed hydrosilylative reduction of secondary amides to amines was achieved utilizing an N , -donor-coordinated cobalt complex as the precatalyst.

Language: Английский

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Hemin‐Promoted Direct C−H Thiolation in the Synthesis of Diaryl Sulfides

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(12)

Published: Feb. 9, 2023

Abstract Diaryl sulfides are a class of important synthetic chemical units. Herein, we report new method for direct preparation diphenyl using P ‐toluenesulfonyl chloride as an effective thiophenyl radical precursor with assistance from Hemin. Various substituted anisoles and benzenesulfonyl chlorides well tolerated, resulting in moderate to good yields diaryl sulfides. The potential the proposed is validated by obtained gram scale reactions.

Language: Английский

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Iron and Base Catalyzed C(α)-Alkylation and One-pot Sequential Alkylation-Hydroxylation of Oxindoles with Secondary Alcohols

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6321 - 6330

Published: Jan. 1, 2024

Iron-catalyzed protocol was developed for the C -alkylation of 2-oxindoles with secondary alcohols as coupling partners. Alkylated were further functionalized to 3-hydroxy-3-alkyl-2-oxindoles by using air most sustainable oxidant.

Language: Английский

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3d-Metal Catalyzed C–C Bond Formation Through α-Alkylation of Ester, Amide, and Nitriles with Alcohol via Dehydrogenative Coupling

Topics in organometallic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 63 - 91

Published: Jan. 1, 2023

Language: Английский

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