Amine-Borane-Mediated, Nickel/Photoredox-Catalyzed Cross-Electrophile Coupling between Alkyl and Aryl Bromides DOI

Ke-Rong Li,

Xian‐Chen He,

Jie Gao

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12658 - 12667

Published: Aug. 19, 2024

Nickel/photoredox catalysis has emerged as a powerful platform for exploring nontraditional and challenging cross-couplings. Herein, metallaphotoredox catalytic protocol been developed on the basis of tertiary amine-ligated boryl radical-induced halogen atom transfer process under blue-light irradiation. A wide variety aryl heteroaryl bromides featuring different functional groups pharmaceutical moieties were facilely coupled to rapidly install C(sp3)-enriched aromatic scaffolds. The compatibility Lewis base-ligated borane with nickel was well exemplified extend chemical space Ni-catalyzed cross-electrophile coupling.

Language: Английский

Light‐Driven Synthesis and Functionalization of Bicycloalkanes, Cubanes and Related Bioisosteres DOI Creative Commons
Sara Cuadros, Julien Paut, Elsa Anselmi

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(14)

Published: Jan. 5, 2024

Bicycloalkanes, cubanes and their structural analogues have emerged as bioisosteres of (hetero)arenes. To meet increasing demand, the chemical community has developed a plethora novel synthetic methods. In this review, we assess progress made in field light-driven construction functionalization such relevant molecules. We focused on diverse targets, well reaction processes giving access to: (i) [1.1.1]-bicyclopentanes (BCPs); (ii) [2.2.1]-bicyclohexanes (BCHs); (iii) [3.1.1]-bicycloheptanes (BCHeps); (iv) cubanes; other structurally related scaffolds. Finally, future perspectives dealing with identification manifolds to new functionalized bioisosteric units are discussed.

Language: Английский

Citations

28

Titanium catalyzed [2σ + 2π] cycloaddition of bicyclo[1.1.0]-butanes with 1,3-dienes for efficient synthesis of stilbene bioisosteres DOI Creative Commons
Yonghong Liu, Zhixian Wu, Jing‐Ran Shan

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 23, 2024

Abstract Natural stilbenes have shown significant potential in the prevention and treatment of diseases due to their diverse pharmacological activities. Here we present a mild effective Ti-catalyzed intermolecular radical-relay [2σ + 2π] cycloaddition bicyclo[1.1.0]-butanes 1,3-dienes. This transformation enables synthesis bicyclo[2.1.1]hexane (BCH) scaffolds containing aryl vinyl groups with excellent regio- trans -selectivity broad functional group tolerance, thus offering rapid access structurally stilbene bioisosteres.

Language: Английский

Citations

22

Enantioselective synthesis of 2-substituted bicyclo[1.1.1]pentanes via sequential asymmetric imine addition of bicyclo[1.1.0]butanes and skeletal editing DOI

Jinteng Che,

Wei‐Yi Ding, Hongbo Zhang

et al.

Nature Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

Language: Английский

Citations

3

Enantioselective photocatalytic synthesis of bicyclo[2.1.1]hexanes as ortho-disubstituted benzene bioisosteres with improved biological activity DOI
Pablo Garrido-García, Irene Quirós, Paula Milán-Rois

et al.

Nature Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 25, 2025

Language: Английский

Citations

3

Facile Synthesis of Housanes by an Unexpected Strategy DOI
Yanyao Liu,

Somanea Tranin,

Yu‐Che Chang

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 17, 2025

Rigid bicyclic hydrocarbons have emerged as important building blocks in the drug discovery industry. Despite progress this general area, bicyclo[2.1.0]pentanes (housanes) are an understudied class of molecules. Herein we report unconventional synthesis borylated housanes. Our method features a broad scope and high diastereoselectivities versatile intermediates. The route involves strain-release diboration bicyclo[1.1.0]butane intramolecular deborylative alkylation. versatility bridgehead boronic ester was demonstrated several functionalizations. Lastly, mechanism reaction investigated, unusual stereospecific diastereoselective ring expansion uncovered.

Language: Английский

Citations

2

Programmable late-stage functionalization of bridge-substituted bicyclo[1.1.1]pentane bis-boronates DOI
Yangyang Yang, Jet Tsien, Ryan Dykstra

et al.

Nature Chemistry, Journal Year: 2023, Volume and Issue: 16(2), P. 285 - 293

Published: Oct. 26, 2023

Language: Английский

Citations

24

Recent advances in C(sp3)–N bond formation via metallaphoto-redox catalysis DOI
Juan Zhang,

Xiao-Die Huan,

Xin Wang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(50), P. 6340 - 6361

Published: Jan. 1, 2024

In this review, the state-of-the-art advances in radical-involved C(sp 3 )–N bond formation via metallaphotoredox catalysis have been highlighted, which are organized according to different catalytic modes, reaction types, and substrate classes.

Language: Английский

Citations

13

Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis DOI Creative Commons
Lauren E. Ehehalt, Omar M. Beleh, Isabella C. Priest

et al.

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

Published: Nov. 26, 2024

Cross-electrophile coupling (XEC), defined by us as the cross-coupling of two different σ-electrophiles that is driven catalyst reduction, has seen rapid progression in recent years. As such, this review aims to summarize field from its beginnings up until mid-2023 and provide comprehensive coverage on synthetic methods current state mechanistic understanding. Chapters are split type bond formed, which include C(sp

Language: Английский

Citations

13

Photochemistry in Medicinal Chemistry and Chemical Biology DOI
Wenyong Zhu, Claire Empel, Sveva Pelliccia

et al.

Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 67(6), P. 4322 - 4345

Published: March 8, 2024

Photochemistry has emerged as a transformative force in organic chemistry, significantly expanding the chemical space accessible for medicinal chemistry. Light-induced reactions enable efficient synthesis of intricate structures and have found applications throughout different stages drug discovery development processes. Moreover, photochemical techniques provide innovative solutions biology, allowing precise spatiotemporal activation targeted delivery. In this Perspective, we highlight already numerous remarkable even more promising future photochemistry chemistry biology.

Language: Английский

Citations

12

(Bio)isosteres of ortho- and meta-substituted benzenes DOI Creative Commons
H Erik Diepers, Johannes C. L. Walker

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 859 - 890

Published: April 19, 2024

Saturated bioisosteres of substituted benzenes offer opportunities to fine-tune the properties drug candidates in development. Bioisosteres

Language: Английский

Citations

10