A three-step strategy for the conversion of pyridines into benzonitriles DOI Creative Commons

Reyhan Güdük,

Niklas Kehl,

Chiara Stavagna

et al.

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

Published: March 7, 2025

Language: Английский

Atomic Carbon Equivalent: Design and Application to Diversity-Generating Skeletal Editing from Indoles to 3-Functionalized Quinolines DOI
Fu‐Peng Wu, Jasper L. Tyler, Constantin G. Daniliuc

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(17), P. 13343 - 13351

Published: Aug. 22, 2024

Atomic carbon and its corresponding masked analogues are exceedingly underexplored intermediates in synthesis. Despite this, these reagents possess inimitable reactivity such as the ability to directly insert atoms into aromatic frameworks while simultaneously generating an additional bond at center further diversify structure. Herein, we report design of orthogonally reactive atomic equivalent Cl-DADO demonstrate application molecular editing indole pyrrole, accessing linchpin-containing ring-expanded heterocycles that can be subsequently derivatized. The value this approach broad applicability reagent highlighted by late-stage skeletal numerous natural products drug molecules.

Language: Английский

Citations

11
Carbon–nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes DOI Creative Commons
Hong Lu, Yu Zhang, Xiuhong Wang

et al.

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

Published: May 4, 2024

Abstract Developing skeletal editing tools is not a trivial task, and realizing the corresponding single-atom transmutation in ring system without altering size even more challenging. Here, we introduce strategy that enables polycyclic arenols, highly prevalent motif bioactive molecules, to be readily converted into N -heteroarenes through carbon–nitrogen transmutation. The reaction features selective nitrogen insertion C–C bond of arenol frameworks by azidative dearomatization aryl migration, followed ring-opening, ring-closing (ANRORC) achieve carbon-to-nitrogen aromatic framework arenol. Using widely available arenols as -heteroarene precursors, this alternative approach allows streamlined assembly complex heteroaromatics with broad functional group tolerance. Finally, pertinent transformations products, including synthesis biheteroarene skeletons, were conducted exhibited significant potential materials chemistry.

Language: Английский

Citations

10
Precision single-atom editing: new frontiers in nitrogen insertion and substitution for the generation of N-heterocycles DOI
Xue Li, Jia Xu, Zhigang Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 4041 - 4053

Published: Jan. 1, 2024

This paper primarily focuses on the editing of nitrogen atoms, encompassing insertion N, substitution C with and utilization 15 N in place 14 for construction N-heterocycles.

Language: Английский

Citations

10
Skeletal Editing of Cyclic Molecules Using Nitrenes DOI

Yi‐An Xu,

Shao‐Hua Xiang,

Jin‐Teng Che

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(21), P. 2656 - 2667

Published: July 16, 2024

Comprehensive Summary Nitrenes, as neutral monovalent nitrogen‐centered molecular species, can insert into various bond or remove nitrogen atoms from amines. Nitrene assisted single‐atom skeletal editing, discovered decades ago, provides an efficient approach for the precise alteration of cyclic skeletons. In this review, we briefly summarize early studies on editing frameworks involving nitrene and introduce several recent important advances systematically.

Language: Английский

Citations

10
A three-step strategy for the conversion of pyridines into benzonitriles DOI Creative Commons

Reyhan Güdük,

Niklas Kehl,

Chiara Stavagna

et al.

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

Published: March 7, 2025

Language: Английский

Citations

2