Triazenolysis of Alkenes: Aza-version of Ozonolysis DOI Creative Commons
Mark Gandelman, Alexander N. Koronatov, Pavel А. Sakharov

и другие.

Research Square (Research Square), Год журнала: 2023, Номер unknown

Опубликована: Окт. 30, 2023

Abstract Numerous applications of alkenes exist due to their abundance and versatility in chemical transformations. In this study, we present a unique novel transformation alkenes, the aza-version canonical ozonolysis reaction, which termed as triazenolysis. This process offers non-trivial previously unfeasible synthetic disconnection, allowing cleavage C=C double bond into two new C-N bonds reductive manner. We carefully examined applicability finding that diverse cyclic are suitable for developed process. Furthermore, an example acyclic alkene, illustrating potential expanding triazenolysis other counterparts. Through DFT calculations, explored mechanism key step demonstrated significance Lewis acid catalysis achieving desired transformation.

Язык: Английский

Photochemical dearomative skeletal modifications of heteroaromatics DOI Creative Commons
Peng Ji, Kuaikuai Duan, Menglong Li

и другие.

Chemical Society Reviews, Год журнала: 2024, Номер 53(12), С. 6600 - 6624

Опубликована: Янв. 1, 2024

Dearomatization has emerged as a powerful tool for rapid construction of 3D molecular architectures from simple, abundant, and planar (hetero)arenes. The field evolved beyond simple dearomatization driven by new synthetic technology development. With the renaissance photocatalysis expansion activation mode, last few years have witnessed impressive developments in innovative photochemical methodologies, enabling skeletal modifications dearomatized structures. They offer truly efficient useful tools facile highly complex structures, which are viable natural product synthesis drug discovery. In this review, we aim to provide mechanistically insightful overview on these innovations based degree alteration, categorized into dearomative functionalization editing, highlight their utilities.

Язык: Английский

Процитировано

12
Copper-catalyzed Larock-type cyclization/debenzylation of yne-allylic esters with aliphatic amines DOI

Rongkang Huang,

Yuepeng Lu,

Feng Xu

и другие.

Science China Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 20, 2025

Язык: Английский

Процитировано

0
Access to Chromenopyrrolidines Enabled by Organophotocatalyzed [2 + 2 + 1] Annulation of Chromones with N-Arylglycines DOI
Xin Zhou, Biwei Zhang,

Ping Wu

и другие.

Organic Letters, Год журнала: 2023, Номер 25(41), С. 7512 - 7517

Опубликована: Окт. 9, 2023

A facile approach toward chromenopyrrolidines was achieved under mild conditions via organophotocatalyzed aerobic decarboxylative [2 + 2 1] annulation of chromones with N-arylglycines, in which N-arylglycines perform dual roles (i.e., radical precursor and methylene provider). Mechanistic studies suggested that a Giese-type addition consequent Mannich pathway were likely responsible for the reaction.

Язык: Английский

Процитировано

8
Three-Component Ring-Expansion Reaction of Indoles Leading to Synthesis of Pyrrolo[2,3-c]quinolines DOI
Jinjin Chen,

Shuxin Jiang,

Weiliang Shi

и другие.

Organic Letters, Год журнала: 2023, Номер 25(37), С. 6886 - 6890

Опубликована: Сен. 7, 2023

Herein, we have developed an atom- and step-economic three-component cascade reaction that enables a modular platform for the synthesis of pyrrolo[2,3-c]quinoline compounds through ring-expansion/cyclization by way novel N1–C2 cleavage indoles. The metal-free catalytic system exhibits broad functional group tolerance.

Язык: Английский

Процитировано

7
Triazenolysis of alkenes as an aza version of ozonolysis DOI
Alexander N. Koronatov, Pavel А. Sakharov, Deepak Ranolia

и другие.

Nature Chemistry, Год журнала: 2024, Номер 17(1), С. 101 - 110

Опубликована: Окт. 11, 2024

Язык: Английский

Процитировано

2
One-Pot Photocascade Catalysis: Access to Pyrrole Derivatives from N-Arylglycines and Morita–Baylis–Hillman (MBH) Acetates DOI

Jie Huang,

S.-L. You,

Ling-Zhi Hu

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 18, 2024

The step-economical synthesis of pyrrole derivatives has posed a challenge in the field

Язык: Английский

Процитировано

1
Triazenolysis of Alkenes: Aza-version of Ozonolysis DOI Creative Commons
Alexander N. Koronatov, Pavel А. Sakharov,

Alexander Kaushansky

и другие.

Опубликована: Окт. 10, 2023

Numerous applications of alkenes exist due to their abundance and versatility in chemical transformations. In this study, we present a unique novel transformation alkenes, the aza-version canonical ozonolysis reaction, which termed as triazenolysis. This process offers non-trivial previously unfeasible synthetic disconnection, allowing cleavage C=C double bond into two new C-N bonds reductive manner. We carefully examined applicability finding that diverse cyclic are suitable for developed process. Furthermore, an example acyclic alkene, illustrating potential expanding triazenolysis other counterparts. Through DFT calculations, explored mechanism key step demonstrated significance Lewis acid catalysis achieving desired transformation.

Язык: Английский

Процитировано

2
Organophotocatalytic pyridination of N-arylglycines with 4-cyanopyridines by decarboxylative and decyanative radical-radical coupling DOI
Changduo Pan,

Chengli Xiang,

Jin‐Tao Yu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(38), С. 7806 - 7810

Опубликована: Янв. 1, 2024

A photocatalytic decarboxylative aminoalkylation of 4-cyanopyridines with

Язык: Английский

Процитировано

0
Divergent Sc(OTf)3‐Catalyzed Tandem Cyclization of o‐Hydroxyphenyl Enaminones with 1,3,5‐Triazinanes: Access to C3‐Aminomethyl Chromones and Tetrahydropyrimidines DOI Open Access

Siyang Han,

Chengcheng Fang, Sifeng Li

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 9, 2024

Abstract A Sc(OTf) 3 ‐catalyzed tandem cyclization reaction of o ‐hydroxyphenyl enaminones with 1,3,5‐triazinanes has been developed to generate two distinct annulated products in moderate good yields, which is dominated by the electronic characteristics 1,3,5‐triazinanes. The 1,3,5‐triaryl‐1,3,5‐triazinane reacted as C−N synthon produce C3‐aminomethyl chromone, while 1,3,5‐trialkyl‐1,3,5‐triazinane acted C−N−C−N synthons deliver N , ‐dialkyl tetrahydropyrimidine a free hydroxyl group.

Язык: Английский

Процитировано

0
Five-membered ring systems: Pyrroles and benzo analogs DOI
Chuan Shan, Justin M. Lopchuk

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 123 - 173

Опубликована: Янв. 1, 2024

Язык: Английский

Процитировано

0