Synthesis of branched and linear aryl allylic alcohols: C H bond allylation of 2-aryl-3H-indoles with vinyl cyclic carbonates DOI
Fan Yu, Bin Li, Xinying Zhang

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 147, P. 155225 - 155225

Published: Aug. 4, 2024

Language: Английский

Synthesis of E-Dienyl Esters Using Acetylene as C2 Synthon DOI
Boxiang Liu,

Zhicong Lin,

Tairan Cheng

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(19), P. 3573 - 3577

Published: May 8, 2023

The stereoselective synthesis of dienyl esters with high atom- and step-economy has been largely unexplored. Herein, we report an efficient approach for the E-dienyl via rhodium catalysis using carboxylic acid acetylene as C2 synthon through cascade cyclometalation C-O coupling. This protocol features mild conditions, excellent functional group tolerance, exclusive E-stereoselectivity utility in late-stage modification pharmaceuticals natural products.

Language: Английский

Citations

6
1,2,4‐Triazines and Calcium Carbide in the Catalyst‐Free Synthesis of 2,3,6‐Trisubstituted Pyridines and Their D‐, 13C‐, and Doubly D2‐13C2‐Labeled Analogues DOI
Vladimir V. Voronin, Mikhail V. Polynski, Maria S. Ledovskaya

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(23)

Published: Oct. 16, 2023

A novel synthetic approach to 2,3,6-trisubstituted pyridines, their 4,5-dideuterated derivatives, 4,5-13 C2 - and doubly-labeled D2 -13 -pyridines has been developed using catalyst-free [4+2] cycloaddition of 1,2,4-triazines in situ generated acetylene or labeled acetylene. Calcium carbide water deuterium oxide were used for the generation dideuteroacetylene. carbide-13 mixture with was applied as 13 -acetylene source.

Language: Английский

Citations

6
Three-Component Gold(I)-Catalyzed Alkoxyvinylation DOI Creative Commons
L. Anders Hammarback,

Tania Medina-Gil,

Anna Sadurní

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6375 - 6379

Published: July 18, 2024

Acetylene has been underexploited despite being a highly valuable feedstock for chemical synthesis. We have developed the first true gold(I)-catalyzed intermolecular three-component reaction between acetylene, alkenes, and alcohols to afford β-vinyl hemiaminal scaffolds from N-vinyl amides. Unusual biscyclopropyl 3-vinyl N-heterocyclic were obtained through incorporation of second unit or tethered alkene into starting material.

Language: Английский

Citations

1
Densely Packed Chemical Synthesis Equipment by 3D Spatial Design and Additive Manufacturing: Acetylene Generation Cartridge DOI
Kirill S. Erokhin, Valentine P. Ananikov

Organic Process Research & Development, Journal Year: 2023, Volume and Issue: 27(6), P. 1144 - 1153

Published: June 7, 2023

Preparation of and carrying out chemical reactions often require considerable laboratory space. Miniaturization equipment reducing space requirements are an essential task to improve cost-efficiency, as well increase safety decrease potential risks. In this work, we discuss the miniaturization through spatial optimization functional parts. To demonstrate this, have optimized size one most cumbersome processes in lab, generation gases from solid sources. We developed a ready-to-use acetylene cartridge with high degree filling internal space, which significantly compacts its dimensions. The was sealed upon three-dimensional (3D) printing, prepacked reagent, found suitable for long-term storage. addition generation, built-in water trap channels drying compartment made it possible obtain dried gas on output cartridge. showed efficiency synthesis bis(arylthio)-substituted ethenes butadienes. expand range products based acetylene, procedure 1,2-bis(alkylthio)ethenes developed. use allowed us target Z-ethenes good yields stereoselectivity.

Language: Английский

Citations

3
Rhodium‐Catalysed Selective C−H Allylation of 1H‐Indazoles with Vinylethylene Carbonate: Easily Introducing Allylic Alcohol DOI
Xiang Zhao,

Junwei Huang,

Yadong Feng

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(40)

Published: Aug. 22, 2023

Abstract An efficient rhodium(III)‐catalysed C−H activation of 3‐aryl‐1‐ H ‐indazoles with easily available vinylethylene carbonate has been reported. A series allyl alcohol substituted were obtained broad functional groups tolerance and favourable stereoselectivity. Notably, C−O bonds selectively activated in “one pot” manner, releasing CO 2 as the sole by‐product avoiding external oxidant. This protocol provides a powerful approach for post stage allylation indazole‐based substrates.

Language: Английский

Citations

2
Enantioselective Allylboration of Acetylene: A Versatile Tool for the Stereodivergent Synthesis of Natural Products DOI Creative Commons
Andrés M. Álvarez‐Constantino, Andrea Chaves‐Pouso, Martín Fañanás‐Mastral

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(34)

Published: June 11, 2024

Abstract Efficient catalytic methods that allow the use of simple and abundant chemical feedstocks for preparation synthetically versatile compounds are central to modern synthetic chemistry. Acetylene is a basic feedstock with remarkable production over one million tons per year, although it underutilized in stereoselective synthesis fine chemicals. Here we report facile multicomponent reaction allows enantio‐ diastereoselective allylboration acetylene gas. This process catalyzed by chiral copper catalyst, operates without specialized equipment or pressurization, provides skipped dienes bearing stereodefined orthogonally functionalized olefins excellent levels chemo‐, regio‐, diastereoselectivity. The combined stereochemical features orthogonal functionalization make products privileged structural scaffolds access complete set stereoisomers diene core through diastereodivergent pathways. utility method demonstrated enantioselective three bioactive natural products, namely (+)‐Nyasol, (+)‐Hinokiresinol Phorbasin C, other related relevant molecules.

Language: Английский

Citations

0
Enantioselective Allylboration of Acetylene: A Versatile Tool for the Stereodivergent Synthesis of Natural Products DOI Creative Commons
Andrés M. Álvarez‐Constantino, Andrea Chaves‐Pouso, Martín Fañanás‐Mastral

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(34)

Published: June 11, 2024

Abstract Efficient catalytic methods that allow the use of simple and abundant chemical feedstocks for preparation synthetically versatile compounds are central to modern synthetic chemistry. Acetylene is a basic feedstock with remarkable production over one million tons per year, although it underutilized in stereoselective synthesis fine chemicals. Here we report facile multicomponent reaction allows enantio‐ diastereoselective allylboration acetylene gas. This process catalyzed by chiral copper catalyst, operates without specialized equipment or pressurization, provides skipped dienes bearing stereodefined orthogonally functionalized olefins excellent levels chemo‐, regio‐, diastereoselectivity. The combined stereochemical features orthogonal functionalization make products privileged structural scaffolds access complete set stereoisomers diene core through diastereodivergent pathways. utility method demonstrated enantioselective three bioactive natural products, namely (+)‐Nyasol, (+)‐Hinokiresinol Phorbasin C, other related relevant molecules.

Language: Английский

Citations

0
Synthesis of branched and linear aryl allylic alcohols: C H bond allylation of 2-aryl-3H-indoles with vinyl cyclic carbonates DOI
Fan Yu, Bin Li, Xinying Zhang

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 147, P. 155225 - 155225

Published: Aug. 4, 2024

Language: Английский

Citations

0