Merging Nucleophilic Phosphine Catalysis and Photocatalysis for the Rapid Assembly of 2-Oxabicyclo-[2.1.1]hexane Scaffolds from Feedstock Allyl Alcohols DOI Creative Commons
David M. Whalley, Luca Carlino, Okky Dwichandra Putra

и другие.

Chemical Science, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

The previously unreported combination of nucleophilic phosphine catalysis and energy transfer allows for the rapid construction structurally distinct 2-oxabicyclo[2.1.1]hexanes (2-oxa-BCH) from readily available building blocks with high atom economy. Previous multistep routes to these important phenyl ring bioisosteres have largely depended on use bespoke strain-release agents or multiple post-functionalisation reactions access structural diversity scaffold. In contrast, this cascade reaction medicinal chemist exploit breadth commercial allyl alcohols synthesise systematically diverse 2-oxa-BCH architectures. Using a polar radical disconnections in same flask, every position scaffold can be substituted useful functional handles such as protected amines, esters alcohols, well arenes alkyl groups. Cyclic even employed yield single diastereomers sp

Язык: Английский

Photoredox-Induced Dearomatization of 2-Alkenyl Aromatic Carboxylic Acids with Terminal Alkynes DOI

Jian‐Peng Cai,

Jiahui Yu, Xiaohui Cao

и другие.

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 9672 - 9681

Опубликована: Май 23, 2025

Язык: Английский

Процитировано

0

Pd/C-Catalyzed Stereoselective Arene Hydrogenation of Benzocyclobutenes Enabled by π-Bond Localization DOI
Zhan Shi, Licheng Lu, Ping Lu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(25), С. 5353 - 5357

Опубликована: Июнь 17, 2024

We developed here a Pd/C-catalyzed diastereoselective

Язык: Английский

Процитировано

2

Drugs from drugs: New chemical insights into a mature concept DOI Creative Commons
Eloy Lozano Baró, Federica Catti,

Carolina Estarellas

и другие.

Drug Discovery Today, Год журнала: 2024, Номер unknown, С. 104212 - 104212

Опубликована: Окт. 1, 2024

Язык: Английский

Процитировано

2

Organophotocatalytic Reduction of Benzenes to Cyclohexenes DOI

K. Uma Devi,

Asad Shehzad, Mario P. Wiesenfeldt

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Дек. 4, 2024

The reduction of abundant benzene rings to scarce C(sp3)-rich motifs is invaluable for drug design, as C(sp3) content known correlate with clinical success. Cyclohexenes are attractive targets, they can be rapidly elaborated into large product libraries and stable against rearomatization. However, partial reactions benzenes cyclohexenes rare have a very narrow scope. Herein we report broadly applicable method that converts electron-poor tolerates Lewis-basic functional groups such triazoles thioethers well reducible cyanides, alkynes, sulfones. reaction utilizes an organic donor induces mild arene by preassociation photoexcitable electron donor–acceptor (EDA) complex isomerization redox-inert 1,4-cyclohexadienes 1,3-cyclohexadienes without strong base in its oxidized thioquinone methide form.

Язык: Английский

Процитировано

2

Modern Dearomative Enlargement of Heteroaromatic Rings DOI
Clément Ghiazza, Xavier Moreau

Synthesis, Год журнала: 2024, Номер 56(20), С. 3119 - 3130

Опубликована: Май 29, 2024

Abstract Breaking aromaticity by inserting additional atoms within the skeleton of heteroaromatic rings has gained significant attention over years. As part emerging concept ‘skeletal editing’, this short review retraces recent progress made on dearomative enlargement reactions both five- and six-membered heterocycles. 1 Introduction 2 Dearomative Enlargement Five-Membered Rings 2.1 Pyrroles, Furans, Thiophenes Their Fused Analogues 2.2 Pyrazoles, Isoxazoles, Isothiazoles 3 Six-Membered 4 Conclusion Perspectives

Язык: Английский

Процитировано

1

Late-Stage Aromatic-Ring Reduction within Drug Molecules DOI
Antonia F. Stepan, Alistair D. Richardson

Synfacts, Год журнала: 2024, Номер 20(07), С. 0752 - 0752

Опубликована: Июнь 14, 2024

Язык: Английский

Процитировано

0

Improving the Photochemical Skeletal Enlargement of Pyridines to 1,2‐Diazepines with Isocyanates DOI
Clément Ghiazza,

Aurélie Damond,

Jérôme Marrot

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Окт. 31, 2024

Abstract In this work, we extend the one‐pot protocol to synthesize 1,2‐diazepines from commercially available and cheap starting materials. Capitalizing on isocyanate derivatives as activating agents, photochemical skeletal enlargement occurs, while preserving key functional groups embedded in more than 30 substrates. We also demonstrated that isocyanates can be generated situ exploiting wealth of methods bench stable resources. Compare previous strategies, use these precursors prevents presence deleterious HCl traces system, thus enabling synthesis high yields over up 5 sequential steps.

Язык: Английский

Процитировано

0

Merging Nucleophilic Phosphine Catalysis and Photocatalysis for the Rapid Assembly of 2-Oxabicyclo-[2.1.1]hexane Scaffolds from Feedstock Allyl Alcohols DOI Creative Commons
David M. Whalley, Luca Carlino, Okky Dwichandra Putra

и другие.

Chemical Science, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

The previously unreported combination of nucleophilic phosphine catalysis and energy transfer allows for the rapid construction structurally distinct 2-oxabicyclo[2.1.1]hexanes (2-oxa-BCH) from readily available building blocks with high atom economy. Previous multistep routes to these important phenyl ring bioisosteres have largely depended on use bespoke strain-release agents or multiple post-functionalisation reactions access structural diversity scaffold. In contrast, this cascade reaction medicinal chemist exploit breadth commercial allyl alcohols synthesise systematically diverse 2-oxa-BCH architectures. Using a polar radical disconnections in same flask, every position scaffold can be substituted useful functional handles such as protected amines, esters alcohols, well arenes alkyl groups. Cyclic even employed yield single diastereomers sp

Язык: Английский

Процитировано

0