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Photosensitization enables Pauson-Khand–type reactions with nitrenes

Titelangaben

Li, Fang ; Zhu, W. Felix ; Empel, Claire ; Datsenko, Oleksandr ; Kumar, Adarsh ; Xu, Yameng ; Ehrler, Johanna H. M. ; Atodiresei, Iuliana ; Knapp, Stefan ; Mykhailiuk, Pavel K. ; Proschak, Ewgenij ; Koenigs, Rene M.:
Photosensitization enables Pauson-Khand–type reactions with nitrenes.
In: Science. Bd. 383 (2024) . - S. 498-503.
ISSN 1095-9203
DOI: https://doi.org/10.1126/science.adm8095

Abstract

The Pauson-Khand reaction has in the past 50 years become one of the most common cycloaddition reactions in chemistry. Coupling two unsaturated bonds with carbon monoxide, the transformation remains limited to CO as a C1 building block. Herein we report analogous cycloaddition reactions with nitrenes as an N1 unit. The reaction of a nonconjugated diene with a nitrene precursor produces bicyclic bioisosteres of common saturated heterocycles such as piperidine, morpholine, and piperazine. Experimental and computational mechanistic studies support relaying of the diradical nature of triplet nitrene into the π-system. We showcase the reaction’s utility in late-stage functionalization of drug compounds and discovery of soluble epoxide hydrolase inhibitors.

Weitere Angaben

Publikationsform: Artikel in einer Zeitschrift
Begutachteter Beitrag: Ja
Institutionen der Universität: Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie
Titel an der UBT entstanden: Nein
Themengebiete aus DDC: 500 Naturwissenschaften und Mathematik > 540 Chemie
Eingestellt am: 28 Mär 2025 07:28
Letzte Änderung: 28 Mär 2025 07:28
URI: https://eref.uni-bayreuth.de/id/eprint/93022