Pd(<scp>II</scp>)‐catalyzed <i>ortho</i>‐Hydroxylation and Intramolecular Oxidative C—C Coupling of <i>N</i>‐Benzylbenzenesulfonamides

Jeong, Eun Joo; Jo, Yoon Hyung; Jang, Min Jung; Youn, So Won

doi:10.1002/bkcs.10126

Cited by 5 publications

References 27 publications

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Development of Synthetic Approaches to Biaryl Sultams via CH Functionalization

Gupta¹,

Laha²

2022

Handbook of CH-Functionalization

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Biaryl sultams represent a privileged molecular scaffold in drug discovery owing to their potential as a clinical candidate. Various developments toward the synthesis of diverse biaryl sultams including metal‐catalyzed and metal‐free CH functionalization involving CC/CN bond formation or annulative cyclization have been advanced in recent time. However, a transition metal‐catalyzed direct CH functionalization approach remains a powerful variant and has been utilized tremendously for the past several decades. The postsynthetic transformations of biaryl sultams to drug‐like molecules offer a tremendous possibility in drug discovery. In this article, we aim to provide an overview of various developments made in the synthetic approaches to biaryl sultams via CH functionalization, with a futuristic emphasis on their postsynthetic utility in accessing (hetero)biaryls containing an ortho ‐sulfonamide or amine functionality, a promising and potentially useful molecular scaffold in therapeutic discovery. The current challenges and a future perspective are also discussed briefly.

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Development of Synthetic Approaches to Biaryl Sultams via CH Functionalization

Gupta¹,

Laha²

2022

Handbook of CH-Functionalization

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Palladium‐Catalyzed Regio‐ and Chemoselective Reactions of 2‐Bromobenzyl Bromides: Expanding the Scope for the Synthesis of Biaryls Fused to a Seven‐Membered Sultam

2015

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Molecules labeled with fluorine‐18 are used as radiotracers for positron emission tomography. An important challenge is the labeling of arenes not amenable to aromatic nucleophilic substitution (SNAr) with [18F]F−. In the ideal case, the 18F fluorination of these substrates would be performed through reaction of [18F]KF with shelf‐stable readily available precursors using a broadly applicable method suitable for automation. Herein, we describe the realization of these requirements with the production of 18F arenes from pinacol‐derived aryl boronic esters (arylBPin) upon treatment with [18F]KF/K222 and [Cu(OTf)2(py)4] (OTf=trifluoromethanesulfonate, py=pyridine). This method tolerates electron‐poor and electron‐rich arenes and various functional groups, and allows access to 6‐[18F]fluoro‐L‐DOPA, 6‐[18F]fluoro‐m‐tyrosine, and the translocator protein (TSPO) PET ligand [18F]DAA1106.

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1,2-Oxazepines and 1,2-Thiazepines

Holtwick

Müller

2022

Comprehensive Heterocyclic Chemistry IV

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Pd(II)‐catalyzed ortho‐Hydroxylation and Intramolecular Oxidative C—C Coupling of N‐Benzylbenzenesulfonamides

Cited by 5 publications

References 27 publications

Development of Synthetic Approaches to Biaryl Sultams via CH Functionalization

Development of Synthetic Approaches to Biaryl Sultams via CH Functionalization

Palladium‐Catalyzed Regio‐ and Chemoselective Reactions of 2‐Bromobenzyl Bromides: Expanding the Scope for the Synthesis of Biaryls Fused to a Seven‐Membered Sultam

1,2-Oxazepines and 1,2-Thiazepines

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Pd(II)‐catalyzed ortho‐Hydroxylation and Intramolecular Oxidative C—C Coupling of N‐Benzylbenzenesulfonamides

Cited by 5 publications

References 27 publications

Development of Synthetic Approaches to Biaryl Sultams via CH Functionalization

Development of Synthetic Approaches to Biaryl Sultams via CH Functionalization

Palladium‐Catalyzed Regio‐ and Chemo­selective Reactions of 2‐Bromobenzyl Bromides: Expanding the Scope for the Synthesis of Biaryls Fused to a Seven‐Membered Sultam

1,2-Oxazepines and 1,2-Thiazepines

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Palladium‐Catalyzed Regio‐ and Chemoselective Reactions of 2‐Bromobenzyl Bromides: Expanding the Scope for the Synthesis of Biaryls Fused to a Seven‐Membered Sultam