Modular access to saturated bioisosteres of anilines via photoelectrochemical decarboxylative C(sp3)–N coupling

Kang-Ning Yuan, Hongjun Zhuang, Jie Wei, Yu Shen, Hong-Qing Yao, Ming-Hong Li, Lin-Lin Xu and Ming Shang ()
Additional contact information
Kang-Ning Yuan: Shanghai Jiao Tong University
Hongjun Zhuang: Xiamen University
Jie Wei: Shanghai Jiao Tong University
Yu Shen: Shanghai Jiao Tong University
Hong-Qing Yao: Shanghai Jiao Tong University
Ming-Hong Li: Shanghai Jiao Tong University
Lin-Lin Xu: Shanghai Jiao Tong University
Ming Shang: Shanghai Jiao Tong University

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: Abstract In drug development, the substitution of benzene rings in aniline-based drug candidates with saturated bridged bicyclic ring systems often enhances pharmacokinetic properties while preserving biological activity. However, current efforts predominantly focuses on bicyclo[1.1.1]pentylamines, accessing analogs capable of mimicking ortho- and meta-substituted anilines remains challenging due to the lack of a versatile and modular synthetic methods. Herein, we present a modular approach to access a diverse array of saturated bioisosteres of anilines via photoelectrochemical-induced decarboxylative C(sp3)–N Coupling. The success of this reaction hinges on the merging the cooperative ligand-to-metal charge transfer (LMCT) with copper-catalyzed amination. Notably, this net-oxidative C(sp3)–N forming reaction operates under mild electrode potentials and proceeds through hydrogen evolution, eliminating the need for external chemical oxidants. Our research enables the facile decarboxylative amination of a set of sp3-rich small-ring cage carboxylic acids, thus offering a versatile bioisosteric replacement for ortho-, meta-, and para-substituted anilines and di(hetero)aryl amines.

Date: 2025
References: View references in EconPapers View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-024-54648-6 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-024-54648-6

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-024-54648-6

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().