Mild and Efficient Cobalt-Catalyzed Cross-Coupling of Aliphatic Amides and Aryl Iodides in Water

Tan, Bryan Yong-Hao; Teo, Yong‐Chua

doi:10.1055/s-0034-1380724

Synlett

2015

DOI: 10.1055/s-0034-1380724

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Mild and Efficient Cobalt-Catalyzed Cross-Coupling of Aliphatic Amides and Aryl Iodides in Water

Bryan Yong-Hao Tan

Yong‐Chua Teo

Abstract: A convenient protocol for the C-N cross-coupling of aliphatic amides and iodobenzene is demonstrated using a simple and inexpensive Co(C 2 O 4 )•2H 2 O/N,N′-dimethylethylenediamine (DMEDA) catalytic system in water. Good yields of N-arylated products were isolated (up to 85%) and the protocol has been successfully applied to the synthesis of the anticancer drug, flutamide.

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Cited by 8 publications

References 10 publications

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Reusable Iron‐Copper Catalyzed Cross‐Coupling of Primary Amides with Aryl and Alkyl Halides: Access to N‐Arylamides as Potential Antibacterial and Anticancer Agents

Roy,

Saha,

Saha

et al. 2024

Chemistry A European J

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We present, for the first time, an efficient ligand‐free iron‐copper catalyzed cross‐coupling reaction involving a variety of aryl, heteroaryl halides (including chlorides, bromides, and iodides), and alkyl bromides with diverse aryl and aliphatic primary amides, conducted under solvent‐minimized conditions. This economically competitive protocol successfully yielded the corresponding cross‐coupling products, N‐arylamides and N‐alkylamides, in good to excellent yields with broad substrate scope (65 examples) and tolerance to several sensitive functionalities (including heterocycles). No conventional work‐up is required for this protocol, and the developed method is applicable for gram‐scale synthesis. Notably, the catalyst is inexpensive, environmentally friendly, and can be reused at least four times with minimal loss of catalytic activity. A series of experiments, including X‐ray photoelectron spectroscopy (XPS), UV spectroscopy, cyclic voltammetry (CV), electron paramagnetic resonance (EPR), and X‐ray diffraction (XRD) were conducted to identify the oxidation state of active catalytic species and radical clock experiment was performed using a radical probe to investigate the reaction mechanism. Furthermore, we evaluated the antibacterial and anticancer properties of selected synthesized products (3ii, 3xii, and 3xxxx) in‐vitro. The results indicated that the prepared compounds exhibited promising antibacterial and anticancer activities (MTT and Molecular Docking).

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Reusable Iron‐Copper Catalyzed Cross‐Coupling of Primary Amides with Aryl and Alkyl Halides: Access to N‐Arylamides as Potential Antibacterial and Anticancer Agents

Roy,

Saha,

Saha

et al. 2024

Chemistry A European J

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ChemInform Abstract: Mild and Efficient Cobalt‐Catalyzed Cross‐Coupling of Aliphatic Amides and Aryl Iodides in Water.

Tan

Teo

2015

ChemInform

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Organophotoredox Pd‐Catalyzed C−H Arylation at Room Temperature using Diaryliodonium Salts

Bennett,

McDonald,

Siddiqui

et al. 2024

ChemPhotoChem

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Direct functionalization of C–H bonds is the most expeditious strategy to build complexity into organic molecules. Unfortunately, most Pd‐catalyzed C–H arylation strategies require high temperatures and/or stoichiometric oxidants. The discovery of metallaphotoredox C–H arylation in 2011 forged a new approach to achieve metal catalyzed C–H arylation at room temperature. Since this discovery, most reports still use explosive diazonium salts as aryl radical precursors. Alternatively, a single report uses bench‐stable diaryliodonium salts, albeit with an Ir‐based photocatalyst. In this study, we develop an organophotoredox manifold that enables Pd‐catalyzed C–H arylation of numerous N‐aryl amide substrates. The results we present are expected to revitalize the use of diaryliodonium salts to achieve room temperature arylations of wide‐ranging classes of C–H bonds.

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Mild and Efficient Cobalt-Catalyzed Cross-Coupling of Aliphatic Amides and Aryl Iodides in Water

Cited by 8 publications

References 10 publications

Reusable Iron‐Copper Catalyzed Cross‐Coupling of Primary Amides with Aryl and Alkyl Halides: Access to N‐Arylamides as Potential Antibacterial and Anticancer Agents

Reusable Iron‐Copper Catalyzed Cross‐Coupling of Primary Amides with Aryl and Alkyl Halides: Access to N‐Arylamides as Potential Antibacterial and Anticancer Agents

ChemInform Abstract: Mild and Efficient Cobalt‐Catalyzed Cross‐Coupling of Aliphatic Amides and Aryl Iodides in Water.

Organophotoredox Pd‐Catalyzed C−H Arylation at Room Temperature using Diaryliodonium Salts

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