Carbon–Nitrogen Transmutation in Polycyclic Arenol Skeletons to Access N-Heteroarenes DOI Creative Commons
Hao Wei

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Фев. 7, 2024

Abstract Developing skeletal editing tools is not a trivial task, and realizing the corresponding single-atom transmutation in ring system without altering size even more challenging. Here, we introduce strategy that enables polycyclic arenols, highly prevalent motif bioactive molecules, to be readily converted into N-heteroarenes through carbon–nitrogen transmutation. The reaction features selective nitrogen insertion C–C bond of arenol frameworks by azidative dearomatization aryl migration, followed opening re-cyclization N,O-hemiketal achieve carbon-to-nitrogen aromatic framework arenol. Using widely available arenols as N-heteroarene precursors, this alternative approach allowed streamlined assembly complex (hetero)aromatics with broad functional group tolerance. This study further highlights potential for sequences combinations other methods, providing an development demonstrating significant materials chemistry.

Язык: Английский

Transition-metal-catalyzed atroposelective synthesis of axially chiral styrenes DOI
Pu‐Fan Qian, Tao Zhou, Bing‐Feng Shi

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(85), С. 12669 - 12684

Опубликована: Янв. 1, 2023

Recent advances in the asymmetric synthesis of axially chiral styrenes catalyzed by transition metals were summarized.

Язык: Английский

Процитировано

43
Carbon–nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes DOI Creative Commons
Hong Lu, Yu Zhang, Xiuhong Wang

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Май 4, 2024

Abstract Developing skeletal editing tools is not a trivial task, and realizing the corresponding single-atom transmutation in ring system without altering size even more challenging. Here, we introduce strategy that enables polycyclic arenols, highly prevalent motif bioactive molecules, to be readily converted into N -heteroarenes through carbon–nitrogen transmutation. The reaction features selective nitrogen insertion C–C bond of arenol frameworks by azidative dearomatization aryl migration, followed ring-opening, ring-closing (ANRORC) achieve carbon-to-nitrogen aromatic framework arenol. Using widely available arenols as -heteroarene precursors, this alternative approach allows streamlined assembly complex heteroaromatics with broad functional group tolerance. Finally, pertinent transformations products, including synthesis biheteroarene skeletons, were conducted exhibited significant potential materials chemistry.

Язык: Английский

Процитировано

10
Photoredox-Catalyzed Hydroacylation of Azobenzenes with Carboxylic Acids DOI
Qiao Li, Jianhui Chen, Yanshu Luo

и другие.

Organic Letters, Год журнала: 2024, Номер 26(7), С. 1517 - 1521

Опубликована: Фев. 12, 2024

Acyl hydrazides are widely found in bioactive compounds and have important applications as versatile synthetic intermediates. In the current report, a photoredox-catalyzed hydroacylation of azobenzenes was disclosed with carboxylic acids acylation reagent, affording variety N,N′-disubstituted hydrazides. The process possesses advantages mild reaction conditions, broad substrate scope, high efficiency. Preliminary mechanistic investigation indicated that addition an acyl radical to azo compound should be involved.

Язык: Английский

Процитировано

4
Nitrene-transfer from azides to isocyanides: Unveiling its versatility as a promising building block for the synthesis of bioactive heterocycles DOI Creative Commons
Devesh M. Sawant, Gaurav Joshi, Arshad J. Ansari

и другие.

iScience, Год журнала: 2024, Номер 27(4), С. 109311 - 109311

Опубликована: Фев. 23, 2024

Cross-coupling azide and isocyanide have recently gained recognition as ideal methods for efficiently synthesizing asymmetric carbodiimides. This reaction exhibits high rates, efficiency, favorable atom/step/redox economy. It enables the nitrene-transfer process, facilitating formation of C-N bonds providing a direct cost-effective synthetic strategy generating diverse These carbodiimides are highly reactive compounds that can undergo

Язык: Английский

Процитировано

4
A Metal-Catalyzed Tunable Reaction of Ylides with Hydroxylamine Derivatives DOI
Honglin Song,

N. F. Chen,

Banpeng Cao

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 25, 2025

In this work, a tunable reaction of metal acyl nitrene with ylides is reported for the divergent synthesis enamides and α,α-dicarbonyl phosphorus ylides. The featured mild conditions, good efficiency, broad generality. particular, resulting could be structurally elaborated into potential useful scaffolds. Mechanism investigation suggests that formation was ascribed to nucleophilic substitution ferric sulfur It believed represents an initial example preparing from iron-catalyzed transfer.

Язык: Английский

Процитировано

0
Chasing isolable late d-block metal nitrenes and imidyls DOI Creative Commons
C. Gunnar Werncke

Dalton Transactions, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

This perspective offers an overview of recent advances in the isolation late d-block metal imidyls and nitrenes related nitridyls metallanitrenes.

Язык: Английский

Процитировано

0
Copper-catalyzed C–N cross-coupling for construction of alkylated N-cyanamide derivatives via nitrogen umpolung DOI
Yanjun Wan,

Harriet K. Zhang,

Jin Qian

и другие.

Chem, Год журнала: 2024, Номер 10(8), С. 2538 - 2549

Опубликована: Май 21, 2024

Язык: Английский

Процитировано

2
Unlocking catalytic potential: a rhodium(II)-based coordination polymer for efficient carbene transfer reactions with donor/acceptor diazoalkanes DOI Creative Commons
Claire Empel,

Marcus N. A. Fetzer,

Suman Sasmal

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(57), С. 7327 - 7330

Опубликована: Янв. 1, 2024

Herein, we report the use of a molecular-defined rhodium( ii ) coordination polymer (Rh-CP) as heterogeneous, recyclable catalyst in carbene transfer reactions.

Язык: Английский

Процитировано

2
Taming Tethered Nitreniums for Alkene Functionalization Reactions DOI Creative Commons
Shyam Sathyamoorthi, R. H. Silver,

Appasaheb Nirpal

и другие.

Опубликована: Июль 23, 2024

Here, we present the first examples of amino-trifluoroacetoxylations alkenes using N-alkoxy carbamate tethers. The trifluoroacetate group can be conveniently removed from product by treatment with a solution NH3 in MeOH. Hypervalent iodine oxidants mediate this transformation, providing “green” alternative to existing intramolecular aminohydroxylation protocols which use toxic metals such as osmium. In all cases examined, reaction is regioselective and stereospecific, geometry starting alkene controlling diastereomeric outcome. By analogy prior art our own observations, posit that transient nitrenium species serves key intermediate transformation.

Язык: Английский

Процитировано

2
Photochemical α-amination of carbonyl groups with iodinanes DOI Creative Commons

Suyuan He,

Boya Feng,

Yiben Tang

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(74), С. 10128 - 10131

Опубликована: Янв. 1, 2024

We report on a photochemical reaction of silyl enol ethers with iminoiodinanes.

Язык: Английский

Процитировано

2