Recent developments in the chemistry of Negishi coupling: a review

Muzammil,; Zahoor, Ameer Fawad; Parveen, Bushra; Javed, Sadia; Akhtar, Rabia; Tabassum, Shaheera

doi:10.1007/s11696-024-03369-7

Chem. Pap.

2024

DOI: 10.1007/s11696-024-03369-7

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Recent developments in the chemistry of Negishi coupling: a review

Muzammil,

Ameer Fawad Zahoor,

Bushra Parveen

et al.

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2024

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Cited by 2 publications

References 76 publications

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Nickel‐Catalyzed Cross‐Coupling of Aryl Alkyl Selenides with Aryl Bromides: Cross‐Coupling Between Two Electrophiles

Kumar,

Sapra,

Singh

2024

Adv Synth Catal

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A nickel‐catalyzed cross‐coupling reaction has been developed using two distinct electrophiles: an aryl alkyl selenide and an aryl bromide. The organoselenium compound, due to the lower bond dissociation energy of the C‐Se bond, acts as a pseudohalide. This one‐pot reaction proceeds by cleaving the C‐Se bond, producing the desired biaryls in moderate to good yields. This method has the potential to become a valuable tool in organic synthesis, owing to its substrate scope and scalability. Importantly, the use of commercially available aryl bromides eliminates the handling of pre‐formed organomagnesium reagents, enhancing the practicality and applicability of this approach.

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Nickel‐Catalyzed Cross‐Coupling of Aryl Alkyl Selenides with Aryl Bromides: Cross‐Coupling Between Two Electrophiles

Kumar,

Sapra,

Singh

2024

Adv Synth Catal

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Negishi-coupling-enabled synthesis of α-heteroaryl-α-amino acid building blocks for DNA-encoded chemical library applications

Gasparetto,

Fődi,

Sipos

2024

Beilstein J. Org. Chem.

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Amino acids are vital motifs in the domain of biochemistry, serving as the foundational unit for peptides and proteins, while also holding a crucial function in many biological processes. Due to their bifunctional character, they have been also used for combinatorial chemistry purposes, such as the preparation of DNA-encoded chemical libraries. We developed a practical synthesis for α-heteroaryl-α-amino acids starting from an array of small heteroaromatic halides. The reaction sequence utilizes a photochemically enhanced Negishi cross-coupling as a key step, followed by oximation and reduction. The prepared amino esters were validated for on-DNA reactivity via a reverse amidation–hydrolysis–reverse amidation protocol.

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Recent developments in the chemistry of Negishi coupling: a review

Cited by 2 publications

References 76 publications

Nickel‐Catalyzed Cross‐Coupling of Aryl Alkyl Selenides with Aryl Bromides: Cross‐Coupling Between Two Electrophiles

Nickel‐Catalyzed Cross‐Coupling of Aryl Alkyl Selenides with Aryl Bromides: Cross‐Coupling Between Two Electrophiles

Negishi-coupling-enabled synthesis of α-heteroaryl-α-amino acid building blocks for DNA-encoded chemical library applications

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