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Visible-Light-Induced [3+2] Cycloadditions of Donor/Donor Diazo Intermediates with Alkenes to Achieve (Spiro)-Pyrazolines and Pyrazoles

Titelangaben

Zhang, Yu ; Li, Yanchuan ; Ni, Shaofei ; Li, Jinpeng ; Xia, Dingding ; Han, Xinyu ; Lin, Jingchuan ; Wang, Jinxin ; Das, Shoubhik ; Zhang, Weidong:
Visible-Light-Induced [3+2] Cycloadditions of Donor/Donor Diazo Intermediates with Alkenes to Achieve (Spiro)-Pyrazolines and Pyrazoles.
In: Chemical Science. Bd. 14 (2023) . - S. 10411-10419.
ISSN 2041-6539
DOI: https://doi.org/10.1039/D3SC04188C

Abstract

The electron donor-acceptor (EDA) complexes has clear advantages to provide complimentary reactivity in organic synthesis while avoiding the need for an expensive transition metal-based photocatalyst. It should be noted that transition metal-based photocatalysts such as Ir- and Ru-complexes have been successfully applied to perform [3+2] cycloaddition reactions for the synthesis of cyclopentane derivatives via the formation of a new C–C bond. Alternatively, we report an EDA complex-mediated strategy to synthesize heterocyclics via the formation of C–N bond. Relying on this strategy, donor/donor diazo compounds were generated in situ. Subsequently, rarely reported (spiro)pyrazolines bearing a quaternary carbon center were afforded via this [3+2] cycloaddition. This protocol exhibited a wide substrate scope, and selective transformations of existing bioactive molecules into functionalized (spiro)pyrazolines analogues were also successfully achieved. Finally, detailed mechanistic investigations proved the formation of the EDA complex and provided a clear mechanistic overview of this reaction.

Weitere Angaben

Publikationsform: Artikel in einer Zeitschrift
Begutachteter Beitrag: Ja
Institutionen der Universität: Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie
Fakultäten
Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften
Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Lehrstuhl Organische Chemie I > Lehrstuhl Organische Chemie I - Univ.-Prof. Dr. Das Shoubhik
Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Lehrstuhl Organische Chemie I
Titel an der UBT entstanden: Nein
Themengebiete aus DDC: 500 Naturwissenschaften und Mathematik > 540 Chemie
Eingestellt am: 11 Sep 2023 07:35
Letzte Änderung: 08 Nov 2023 11:23
URI: https://eref.uni-bayreuth.de/id/eprint/86824