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

Unveiling N-Fused Nitreniums as Potent Catalytic Photooxidants DOI

Samim Sohel Rana,

Joyanta Choudhury

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(6), С. 3603 - 3608

Опубликована: Янв. 31, 2024

The first example of a hitherto-unknown facet catalytic photooxidant capability nitrenium cations is reported herein. fundamental limitation inability the traditional and nitreniums to achieve excited-state redox potential beyond +2.0 V (vs Ag/AgCl), primary requirement for powerful photooxidant, addressed in this work by developing structurally unique class N-fused cations, with required structural engineering involving extensive π-conjugation through ring fusion at site, which enabled significant lowering LUMO energy easy reduction excited state (excited-state up +2.5 vs facilitated effective delocalization/stabilization generated radical. This finding opens new way discover novel useful (photo)catalytic properties just Lewis acidity.

Язык: Английский

Процитировано

11
N-Heterocyclic Nitrenium-Catalyzed Photohomolysis of CF3SO2Cl for Alkene Trifluoromethylation DOI

Xiaojian Ren,

Peng-Wei Liao,

Sheng He

и другие.

Organic Letters, Год журнала: 2023, Номер 25(33), С. 6189 - 6194

Опубликована: Авг. 14, 2023

N-Heterocyclic nitreniums (NHNs) have been utilized as Lewis acid catalysts to activate substrates with lone pairs. Alternative their conventional applications, we discovered that NHNs can also serve charge transfer complex catalysts. Herein, present another potential of by utilizing a weak interaction between and CF3SO2Cl. The method promotes CF3SO2Cl undergo photohomolysis, resulting in the CF3 radical. Mechanistic studies suggested could be due π-hole effect NHNs.

Язык: Английский

Процитировано

14
Photoredox-catalyzed C-heteroaryl glycosylation of biphenyl isocyanides with glycosyl bromides DOI

Yi Jiao,

Xiaoran Shi, Shouyun Yu

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(89), С. 13336 - 13339

Опубликована: Янв. 1, 2023

Reported here is a strategy to access C-heteroaryl glycosides by photoredox catalysis. C6-Glycosylated phenanthridine derivatives are synthesized from biphenyl isocyanides and glycosyl bromides.

Язык: Английский

Процитировано

12
Photoinduced N-heterocyclic nitrenium-catalyzed single electron reduction of Se–Se bond for the generation of nucleophilic selenolates DOI
Chaoshen Zhang,

Kun‐Quan Chen,

Ling Zhou

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(7), С. 2070 - 2074

Опубликована: Янв. 1, 2024

A straightforward photoinduced NHN-catalyzed method for generating nucleophilic selenolates from diselenides without the need of stoichiometric reductants.

Язык: Английский

Процитировано

4
N-Heterocyclic nitrenium-catalyzed photoreductive radical-polar crossover for alkene dicarbofunctionalization DOI Creative Commons

Youfeng Han,

Beibei Zhang, Zhixiang Wang

и другие.

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Март 1, 2024

The photoredox radical-polar crossover paradigm is a valuable tool for 1,2-difunctionalization of alkenes. However, the use unactivated alkyl halides as radical precursors remains far less developed. Here, we report photoreductive N-heterocyclic nitrenium-catalyzed 1,2-dicarbofunctionalization alkenes by using and aryl iodides. These reactions can be carried out under simple, transition-metal-free conditions with easily obtainable materials such alkyl/aryl halides, alkenes, aldehydes. exhibit broad range substrate compatibility good tolerance towards functional groups. This approach offers new to unlock carbon skeletons.

Язык: Английский

Процитировано

3
Recent Advances in Combining Photo- and N-Heterocycle Nitrenium Catalysis DOI

Yongliang Tu,

Xiangyu Chen, Xiang Li

и другие.

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Сен. 19, 2024

Abstract N-Heterocyclic nitreniums (NHNs) are isoelectronic and isostructural analogues of N-heterocyclic carbenes (NHCs). Unlike NHCs, NHNs much less developed. While a comprehensive understanding NHN reactivity remains elusive, recent advancements have demonstrated their utility as Lewis acid catalysts, photoreductants, photooxidants, leading to several reaction patterns. In this short review, we focus on the applications in photoredox reactions. We also discuss mechanisms behind these transformations outline future research directions. 1 Introduction 2 Application Nitreniums Photoreductants 3 Facilitate Photohomolysis 4 Photooxidants 5 Conclusion

Язык: Английский

Процитировано

3
N-Heterocyclic nitrenium-catalyzed triple domino reaction of organic iodides for the synthesis of phthalides and δ-lactones DOI Creative Commons
Xin Wang, Sixian Wang, Weige Zhang

и другие.

Green Synthesis and Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Апрель 1, 2025

Язык: Английский

Процитировано

0
Photoinduced N‑Heterocyclic Nitrenium-Catalyzed Single Electron Reduction of α-Chloro Esters for Phenanthridine Synthesis DOI
Ling Zhou,

Xue‐Feng Pei,

Wei Gong

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

An efficient photoactive charge transfer complex protocol for the synthesis of phenanthridine derivatives by reaction 2-isocyanobiaryls with α-chloro esters is established.

Язык: Английский

Процитировано

0
Visible Light‐Induced N‐Heterocyclic Nitrenium‐Catalyzed Deoxygenative Borylation of Acyl Chlorides DOI Creative Commons

Rahul Mondal,

Apurba Kumar Pal,

K. Geetharani

и другие.

ChemistryEurope, Год журнала: 2025, Номер unknown

Опубликована: Июнь 1, 2025

Considering the appealing synthetic properties of oxygenous feedstocks and organoboron compounds, direct deoxygenative borylation is a very desirable chemical transformation. Directly converting acyl chlorides into alkylboronates through an unknown but valuable reaction. Herein, relatively straightforward one‐step methodology reported where N‐heterocyclic nitrenium (NHN) ion acts as photocatalyst under visible light to produce benzylboronates directly from aroyl in absence metals or additives. A large variety are well tolerated reaction conditions. Mechanistic investigations density functional theory calculations support that NHN species involved radical formation DMAc‐H 2 O/B cat contributes alkylboronates.

Язык: Английский

Процитировано

0
N-heterocyclic nitrenium charge transfer catalysis via inner-sphere electron transfer in concert with halogen-atom dissociation DOI
Chaoshen Zhang,

Chang-Zhen Fang,

Yi Liang

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(3), С. 673 - 683

Опубликована: Ноя. 28, 2023

We report an efficient and versatile catalytic N-heterocyclic nitrenium charge transfer complex strategy for the single-electron reduction of chloroform, resulting in generation dichloromethyl radical use various transformations.

Язык: Английский

Процитировано

7