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

et al.

Research Square (Research Square), Journal Year: 2023, Volume and Issue: unknown

Published: Oct. 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.

Language: Английский

Dearomative Ring-Opening of N-Fused Heteroarenes: Access to Tetrasubstituted Alkenes and Ketimines DOI

Qianling Wu,

Xiaojing Wang, Qijian Ni

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 15, 2025

We report a novel and efficient strategy for constructing tetrasubstituted alkenes α-iminonitriles from 3-aminoindolizines 3-aminoimidazo[1,2-a]pyridines. This approach involves dearomative ring-opening of N-fused heteroaromatic amines coupled to DDQ-mediated oxidative process under mild, metal-free conditions. The methodology demonstrates broad substrate scope, excellent functional group tolerance, scalability, offering versatile platform synthesizing complex nitrile-containing frameworks.

Language: Английский

Citations

0
Total Synthesis of Alanense A through an Intramolecular Friedel–Crafts Alkylation DOI
Kosho Makino,

Rio Fukuda,

Shunsuke Sueki

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 2050 - 2054

Published: Jan. 19, 2024

The first total synthesis of cadinane sesquiterpenoid alanense A, in which an intramolecular dehydrative Friedel–Crafts alkylation 2,5-diaryl-2-pentanol is incorporated as a key step, has been achieved. combinatorial use p-TsOH·H2O catalyst and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) solvent provides 1,1-disubstituted tetrahydronaphthalene 97% yield. It was also found that the combination p-TsOH HFIP effective for removal phenolic MOM ether.

Language: Английский

Citations

3
Triazenolysis of alkenes as an aza version of ozonolysis DOI
Alexander N. Koronatov, Pavel А. Sakharov, Deepak Ranolia

et al.

Nature Chemistry, Journal Year: 2024, Volume and Issue: 17(1), P. 101 - 110

Published: Oct. 11, 2024

Language: Английский

Citations

2
Formal One Carbon Deletion of Indoline Hemiaminals under Tautomeric Control to Access 2-Aminobenzyl Compounds DOI
Keisuke Tokushige, Takumi Abe

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10349 - 10354

Published: July 1, 2024

Unprecedented tert-BuOK-mediated one carbon deletion of indoline hemiaminals has been achieved. This novel protocol provides an efficient synthetic tool for the construction 2-aminobenzyl compounds with high chemoselectivity. In addition, functionalized are difficult to make, which few limited means access currently exist. The key success is use in situ generated Heyns rearrangement products (α-amino carbonyl compounds) as precursors formal deletion.

Language: Английский

Citations

1
Brønsted Acid-Catalyzed Dehydrative Nazarov-type Cyclization of CF3-Substituted 3-Indolylallyl Alcohols: Divergent Synthesis of 1-Trifluoromethylated Cyclopenta[b]indoles DOI

Yuling Teng,

Xiangdong Yu,

Dandan Shang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(2), P. 1147 - 1159

Published: Jan. 4, 2024

An expedient and efficient synthetic method for the divergent synthesis of 1-trifluoromethylated cyclopenta[b]indoles that relies on Brønsted acid-catalyzed dehydrative Nazarov-type cyclization CF3-substituted 3-indolylallyl alcohols is described. Two classes can be easily accessed simply by changing NH-protecting group indoles. With arylsulfonyl protected as starting materials, reaction provided in good to excellent yields, whereas pivaloyl (Piv) substrates led formation NH-free cyclolopenta[b]indoles with another alkenyl isomer. This protocol features tunable chemoselectivity, operational simplicity, functional compatibility, mild metal-free conditions.

Language: Английский

Citations

1
Ring-opening silylation of N-arylindoles via endocyclic C−N bond cleavage triggered by silylboranes DOI
Ye Tian,

Hanying Sun,

Benqiang Cui

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Ring-opening silylation of indoles via reductive activation triggered by electron-rich silylboronic complexes has been successfully developed to produce silyl styrenes with perfect stereoselectivity.

Language: Английский

Citations

0
Thiophene and benzo[b]thiophene DOI

Sean Chin Chan,

Andrii Monastyrskyi

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 89 - 122

Published: Jan. 1, 2024

Language: Английский

Citations

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

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 123 - 173

Published: Jan. 1, 2024

Language: Английский

Citations

0
Triazenolysis of Alkenes: Aza-version of Ozonolysis DOI Creative Commons
Mark Gandelman, Alexander N. Koronatov, Pavel А. Sakharov

et al.

Research Square (Research Square), Journal Year: 2023, Volume and Issue: unknown

Published: Oct. 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.

Language: Английский

Citations

0