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

Nitrenium ions as new versatile reagents for electrophilic amination DOI Creative Commons
Idan Avigdori, Kuldeep Singh, Natalia Fridman

и другие.

Chemical Science, Год журнала: 2023, Номер 14(43), С. 12034 - 12040

Опубликована: Янв. 1, 2023

Bench-stable N-heterocyclic nitrenium ions were used for the efficient electrophilic amination of organometallic nucleophiles. The previously unexplored N -alkyl/aryl triazane intermediates reduced to produce a diverse scope primary amines.

Язык: Английский

Процитировано

4
Unified Approach to Diverse Heterocyclic Synthesis: Organo-Photocatalyzed Carboacylation of Alkenes and Alkynes from Feedstock Aldehydes and Alcohols DOI
Vishal Jyoti Roy, Neha Dagar, Swagata Choudhury

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(21), С. 15374 - 15388

Опубликована: Окт. 23, 2023

We report an organo-photocatalyzed carboacylation reaction that offers a springboard to create chemical complexity in diversity-driven approach. The modular one-pot method uses feedstock aldehydes and alcohols as acyl surrogates commercially available Eosin Y the photoredox catalyst, making it simple affordable introduce structural diversity. Several biologically relevant skeletons have been easily synthesized under mild conditions presence of visible light irradiation by fostering radical acylation/cyclization cascade. proposed mechanism was further illuminated number spectroscopic studies. Furthermore, we applied this protocol for late-stage functionalization pharmaceuticals blockbuster drugs.

Язык: Английский

Процитировано

4
NHC-Catalyzed Tandem Reaction: A Strategy for the Synthesis of 2-Pyrrolidinone-Functionalized Phenanthridines DOI
Nengneng Zhou, Lei Wang,

Fangli Zhao

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16556 - 16565

Опубликована: Ноя. 16, 2023

Herein, an N-heterocyclic carbene (NHC)-catalyzed tandem cyclization/addition/cyclization reaction of 2-isocyanobiaryls and α-bromo-N-cinnamylamides for the synthesis 2-pyrrolidinone-functionalized phenanthridines is developed. This protocol features a radical cascade process, broad substrate scope, good functional group compatibility under metal- oxidant-free conditions.

Язык: Английский

Процитировано

4
Multimodal Molecular Motion in the Rotaxanes and Catenanes Incorporating Flexible Calix[n]phyrin Stations DOI Creative Commons
Rafał A. Grzelczak, Tymoteusz Basak, Bartosz Trzaskowski

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 64(1)

Опубликована: Авг. 27, 2024

The synthesis of [2]rotaxanes stoppered with one or two dipyrromethane groups has opened a route for the construction mechanically interlocked molecules incorporating various porphyrinoid stations. exploitation those precursors allowed creation [3]rotaxanes and [2]catenanes based on calix[4]phyrin motif, presenting intriguing molecular dynamics. intrinsic flexibility introduction new type motion within rotaxanes, termed fluttering. latter involved bending axle, interconverting angular-shaped stereoisomers rotaxane through planarised transition state. Simple chemical transformations, i.e. methylation (de)protonation [3]rotaxane [2]catenane controllable transformations conformationally flexible calix[4]phyrin-incorporated porphyrinoids.

Язык: Английский

Процитировано

1
Organocatalyzed iodine-mediated reversible-deactivation radical polymerization via photoinduced charge transfer complex catalysis DOI
Xiang Li, Beibei Zhang, Zhixiang Wang

и другие.

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110383 - 110383

Опубликована: Авг. 1, 2024

Язык: Английский

Процитировано

1
Metal-Free Photoinduced-Radical Hydrocyclization of 2-Isocyanides: A Unified Synthetic Approach to Facilely Assemble Diverse N-Heteroarenes DOI
Ziyi Wang,

Haonan Wei,

Jinrong Du

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(21), С. 10804 - 10810

Опубликована: Янв. 1, 2024

We present an efficient and sustainable protocol for the photoinduced-radical hydrocyclization of isocyanides, providing a united route to assemble diverse α-unsubstituted N-heteroarenes.

Язык: Английский

Процитировано

1
N-Heterocyclic nitrenium catalyzed photosynthesis of 3,3-disubstituted oxindoles from α-chloroanilides DOI

Kun‐Quan Chen,

Jia Zhang,

Dequn Sun

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 5, 2024

A photoinduced N-heterocyclic nitrenium-catalyzed strategy for the synthesis of 3,3-oxindoles from α-chloroanilides under transition-metal-free conditions was reported.

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
Visible‐Light‐Driven Synthesis of 6‐Aroyl Benzimidazo[1,2‐c]quinazolines from N‐Cyanobenzimidazoles and α‐Keto Acids by Radical Relay Cyclization DOI

Yang Hu,

Cheng‐Liang Liu,

Wen‐Tao He

и другие.

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

Опубликована: Май 31, 2024

Abstract A diverse array of 6‐aroyl benzimidazo[1,2‐ c ]quinazolines was successfully synthesized using easily obtainable N ‐cyanobenzimidazoles and α‐keto acids, facilitated by photoredox catalysis. mechanistic investigation revealed that this methodology might involve both energy transfer catalytic cycles, generating acyl radicals subsequently promote radical relay cyclization.

Язык: Английский

Процитировано

0
Multimodal Molecular Motion in the Rotaxanes and Catenanes Incorporating Flexible Calix[n]phyrin Stations DOI Creative Commons
Rafał A. Grzelczak, Tymoteusz Basak, Bartosz Trzaskowski

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 137(1)

Опубликована: Авг. 27, 2024

Abstract The synthesis of [2]rotaxanes stoppered with one or two dipyrromethane groups has opened a route for the construction mechanically interlocked molecules incorporating various porphyrinoid stations. exploitation those precursors allowed creation [3]rotaxanes and [2]catenanes based on calix[4]phyrin motif, presenting intriguing molecular dynamics. intrinsic flexibility introduction new type motion within rotaxanes, termed fluttering. latter involved bending axle, interconverting angular‐shaped stereoisomers rotaxane through planarised transition state. Simple chemical transformations, i.e. methylation (de)protonation [3]rotaxane [2]catenane controllable transformations conformationally flexible calix[4]phyrin‐incorporated porphyrinoids.

Язык: Английский

Процитировано

0