Chemoselective silver-catalyzed nitrene transfer: Tunable syntheses of azepines and cyclic carbamimidates DOI Creative Commons

Emily Schroeder,

Chenxi Lin,

Zhen-Yao Dai

и другие.

Опубликована: Июнь 19, 2024

Azepines and their saturated azepane counterparts are important moieties in bioactive molecules but underrepresented current drug screening libraries. Herein, we report a mild efficient azepine formation via silver-catalyzed dearomative nitrene transfer. A 2,2,2-trichloroethoxysulfonyl (Tces)-protected carbamimidate precursor, coupled with the appropriate ligand for silver, is essential achieving unexpected chemoselectivity between arene dearomatization benzylic C(sp3)–H amination. Potential applications late-stage diversification of azepines to complex molecular scaffolds diastereoselective hydrogenations high Fsp3 azepanes also highlighted.

Язык: Английский

Skeletal Editing via Transition‐Metal‐Catalyzed Nitrene Insertion DOI

Pratibha Bhatti,

Anjali Gupta, Shubham Chaudhari

и другие.

The Chemical Record, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 28, 2024

Abstract Metal‐nitrenes are valuable reactive intermediates for synthesis and widely used to construct biologically relevant scaffolds, complexes functionalized molecules. The ring expansion of cyclic molecules via single‐nitrogen‐atom insertion nitrene or metal‐nitrenoid has emerged as a promising modern strategy driving advantageous nitrogen‐rich compound synthesis. In recent years, the catalytic single nitrogen atom into carbocycles, leading N‐heterocycles, become an important focus synthetic approaches with applications in medicinal chemistry, materials science, industry. Catalytic insertions have been increasing prominence organic due their capability high‐value added nitrogen‐containing heterocycles from simple feedstocks. this review, we will discuss rapidly growing field skeletal editing using transition metal catalysis access heterocycles, on across wide spectrum carbocycles.

Язык: Английский

Процитировано

2
Single-Carbon Insertion into Single C–C Bonds with Diazirines DOI Creative Commons

Valero G. Alfonso,

Karen de la Vega‐Hernández, Marcos G. Suero

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Дек. 16, 2024

A novel platform for the skeletal editing of single C–C bonds via a single-carbon insertion has been developed using diazirines. This strategy involves photogeneration arylchlorocarbenes as carbynoid species that undergo site-selective carbene into tertiary C–H and subsequent Wagner–Meerwein rearrangement promoted by silver salt. Our based on formal selective carbyne bond demonstrated in six core-to-core conversions, including linear cyclic benzylic substrates, alkanes late-stage functionalizations.

Язык: Английский

Процитировано

2
Selective Ring‐Opening Amination of Isochromans and Tetrahydroisoquinolines DOI

Changhao Niu,

Zheng Zhang, Qi Li

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(17)

Опубликована: Март 9, 2024

Abstract The molecular structure‐editing through selective C−C bond cleavage allows for the precise modification of structures and opens up new possibilities in chemical synthesis. By strategically cleaving bonds editing structure, more efficient versatile pathways synthesis complex compounds could be designed, which brings significant implications drug development materials science. o ‐Aminophenethyl alcohols amines are essential key motifs bioactive functional material molecules. traditional these usually requires multiple steps generate inseparable isomers induce low efficiencies. leveraging a strategy, we herein reported ring‐opening amination isochromans tetrahydroisoquinolines ‐aminophenethyl amines. This innovative chemistry under mild transition metal‐free conditions. Notably, further synthetic application demonstrated that our method provide an approach to components diverse

Язык: Английский

Процитировано

1
Modern Dearomative Enlargement of Heteroaromatic Rings DOI
Clément Ghiazza, Xavier Moreau

Synthesis, Год журнала: 2024, Номер 56(20), С. 3119 - 3130

Опубликована: Май 29, 2024

Abstract Breaking aromaticity by inserting additional atoms within the skeleton of heteroaromatic rings has gained significant attention over years. As part emerging concept ‘skeletal editing’, this short review retraces recent progress made on dearomative enlargement reactions both five- and six-membered heterocycles. 1 Introduction 2 Dearomative Enlargement Five-Membered Rings 2.1 Pyrroles, Furans, Thiophenes Their Fused Analogues 2.2 Pyrazoles, Isoxazoles, Isothiazoles 3 Six-Membered 4 Conclusion Perspectives

Язык: Английский

Процитировано

1
Chemoselective silver-catalyzed nitrene transfer: Tunable syntheses of azepines and cyclic carbamimidates DOI Creative Commons

Emily Schroeder,

Chenxi Lin,

Zhen-Yao Dai

и другие.

Опубликована: Июнь 19, 2024

Azepines and their saturated azepane counterparts are important moieties in bioactive molecules but underrepresented current drug screening libraries. Herein, we report a mild efficient azepine formation via silver-catalyzed dearomative nitrene transfer. A 2,2,2-trichloroethoxysulfonyl (Tces)-protected carbamimidate precursor, coupled with the appropriate ligand for silver, is essential achieving unexpected chemoselectivity between arene dearomatization benzylic C(sp3)–H amination. Potential applications late-stage diversification of azepines to complex molecular scaffolds diastereoselective hydrogenations high Fsp3 azepanes also highlighted.

Язык: Английский

Процитировано

1