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

Title data

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. Vol. 14 (2023) . - pp. 10411-10419.
ISSN 2041-6539
DOI: https://doi.org/10.1039/D3SC04188C

Abstract in another language

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.

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I > Chair Organic Chemistry I - Univ.-Prof. Dr. Das Shoubhik
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 11 Sep 2023 07:35
Last Modified: 08 Nov 2023 11:23
URI: https://eref.uni-bayreuth.de/id/eprint/86824