Synthesis of 1-Substituted Bicyclo[2.1.1]hexan-2-ones via a Sequential SmI2-Mediated Pinacol Coupling and Acid-Catalyzed Pinacol Rearrangement Reaction DOI Creative Commons

Yung‐Chi Lee,

Yi-Chen Chen,

Chunfu Wu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9352 - 9356

Published: Oct. 22, 2024

A two-step procedure, combining a SmI

Language: Английский

1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of ortho-substituted benzene DOI Creative Commons

Aleksandr Denisenko,

Pavel Garbuz,

Yelyzaveta Makovetska

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(48), P. 14092 - 14099

Published: Jan. 1, 2023

1,2-Disubstituted bicyclo[2.1.1]hexanes have been synthesized, characterized, and biologically validated as saturated bioisosteres of the ortho -substituted benzene ring.

Language: Английский

Citations

46

Reaction Paradigms that Leverage Cycloaddition and Ring Strain to Construction Bicyclic Aryl Bioisosteres from Bicyclo[1.1.0]butanes DOI

Stephen J. Sujansky,

Xiaoshen Ma

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(5)

Published: Feb. 21, 2024

Abstract Within a medicinal chemist's toolbox, one of the most effective strategies to improve overall properties biologically active compound is bioisosteric replacement. Ever since first example replacing benzene with bicyclo[1.1.1]pentane (BCP) group was published in late 1990s, [1] chemistry community has continually been expanding scope such phenyl replacements. Recent interest from academia focused on novel synthetic access C( sp 3 )‐rich bicyclic hydrocarbons expanded ring sizes. Herein, we summarize some these transformations and reveal that rely strain releasing cycloadditions bicyclo[1.1.0]butane (BCB) bicyclo[2.1.0]pentane (housane). We have organized this review based mechanism release strategies, namely, carbene cycloadditions, energy transfer photocatalyzed electron catalyzed polar cycloadditions.

Language: Английский

Citations

29

Palladium-catalyzed decarboxylative (4 + 3) cycloadditions of bicyclobutanes with 2-alkylidenetrimethylene carbonates for the synthesis of 2-oxabicyclo[4.1.1]octanes DOI Creative Commons

X. N. Gao,

Lei Tang, Xu Zhang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(34), P. 13942 - 13948

Published: Jan. 1, 2024

While cycloaddition reactions of bicyclobutanes (BCBs) have emerged as a potent method for synthesizing (hetero-)bicyclo[

Language: Английский

Citations

23

Challenges and Future Perspectives in Photocatalysis: Conclusions from an Interdisciplinary Workshop DOI Creative Commons
Sebastian B. Beil, Sylvestre Bonnet, Carla Casadevall

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(8), P. 2746 - 2766

Published: Aug. 8, 2024

Photocatalysis is a versatile and rapidly developing field with applications spanning artificial photosynthesis, photo-biocatalysis, photoredox catalysis in solution or supramolecular structures, utilization of abundant metals organocatalysts, sustainable synthesis, plastic degradation. In this Perspective, we summarize conclusions from an interdisciplinary workshop young principal investigators held at the Lorentz Center Leiden March 2023. We explore how diverse fields within photocatalysis can benefit one another. delve into intricate interplay between these subdisciplines, by highlighting unique challenges opportunities presented each multidisciplinary approach drive innovation lead to solutions for future. Advanced collaboration knowledge exchange across domains further enhance potential photocatalysis. Artificial photosynthesis has become promising technology solar fuel generation, instance, via water splitting CO

Language: Английский

Citations

17

Coulomb interactions for mediator-enhanced sensitized triplet–triplet annihilation upconversion in solution DOI
Felix Glaser, Matthias Schmitz, Christoph Kerzig

et al.

Nanoscale, Journal Year: 2023, Volume and Issue: 16(1), P. 123 - 137

Published: Nov. 29, 2023

An energy transfer cascade in a three-component upconversion system improves the emission quantum yield and reduces intrinsic filter effects. Investigations of molecular interactions are combined with lab-scale applications photocatalysis.

Language: Английский

Citations

10

Regioselective difluoroallylation of alkylidene malonates with trifluoromethyl alkenes: synthesis of gem-difluoro-1,5-dienes and their [2 + 2] photocycloaddition DOI
Weidi Zeng, Mingqiang Li,

Shaofeng Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(12), P. 3421 - 3426

Published: Jan. 1, 2024

The synthesis of gem -difluoro-1,5-dienes via regioselective S N 2′-type reactions alkylidene malonates with trifluoromethyl alkenes and their subsequent [2 + 2] photocycloaddition for the formation bicyclo[2.1.1]hexanes are described.

Language: Английский

Citations

2

Aqueous Micellar Environment Impacts the Co-Catalyzed Phototransformation: A Case Study DOI Creative Commons
Aleksandra Wincenciuk, Piotr Cmoch, Maciej Giedyk

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(29), P. 19828 - 19838

Published: July 9, 2024

In recent years, methodologies that rely on water as the reaction medium have gained considerable attention. The unique properties of micellar solutions were shown to improve regio-, stereo-, and chemoselectivity different transformations. Herein, we demonstrate aqueous environment is a suitable for visible light driven cobalt-catalyzed involving radical species. this system, reduced vitamin B

Language: Английский

Citations

2

UV‐Light Generation in Micelles via Triplet‐Triplet Annihilation Upconversion – Towards Synthetic Applications DOI Creative Commons

Rubaishan Jeyaseelan,

Martin Utikal,

Line Næsborg

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(3)

Published: Jan. 10, 2024

Abstract Over the last century UV‐light mediated processes gave access to synthetically valuable products. Some of disadvantages encountered when performing such triggered synthetic reactions are necessity for special glassware (quartz), environmentally unfriendly irradiation sources and need oxygen removal, often via time consuming freeze‐pump‐thaw cycles. In addition, penetration into reaction mixture is a challenge due absorption effects scattering. A solution these could be triplet‐triplet annihilation upconversion performed under micellar conditions. Hereby, can generated in using visible light irradiation. aqueous medium allow process occur without removal. This concept has been sporadically demonstrated holds great promise development promoted photochemical milder more benign conditions that may eventually scale up protocols.

Language: Английский

Citations

1

Avoiding Oxygen Removal for Photochemical Reactions – towards Water as the Solvent DOI Creative Commons

Gianna Pölderl,

Line Næsborg

ChemPhotoChem, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 23, 2024

Abstract Oxygen removing protocols have long been the standard approach to perform photoreactions. By encapsulating photosensitizers and reactants in tailored supramolecular assemblies, preservation of photoreactivity even presence molecular oxygen can be observed. Herein, we showcase some solutions that could render time‐consuming removal redundant photochemical synthesis. A focus has dedicated aqueous assemblies as potential reaction media. They present an attractive solution possibly useful not only for synthetic transformations, but also water purification, bio‐applications or biocatalysis. The included media are membranes, hydrogels, deep eutectic solvents peptide assemblies.

Language: Английский

Citations

1

Aqueous Micellar Environment Impacts the Co-Catalyzed Phototransformation: A Case Study DOI Creative Commons
Aleksandra Wincenciuk, Piotr Cmoch, Maciej Giedyk

et al.

Published: Feb. 20, 2024

In recent years, methodologies that rely on water as the reaction medium have gained considerable attention. The unique properties of micellar solutions were shown to improve regio-, stereo-, and chemoselectivity different transformations. Herein, we demonstrate aqueous environment is a suitable for visible light driven cobalt-catalyzed involving radical species. this system, reduced vitamin B12 reacts with alkyl halides, gen-erating radicals are trapped by lipophilic olefin present in Stern layer. A series NMR measurements theoretical studies revealed location components system.

Language: Английский

Citations

1