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Norcaradiene Synthesis via Visible-Light-Mediated Cyclopropanation Reactions of Arenes

Title data

Guo, Yujing ; Nguyen, Thanh Vinh ; Koenigs, Rene M.:
Norcaradiene Synthesis via Visible-Light-Mediated Cyclopropanation Reactions of Arenes.
In: Organic Letters. Vol. 21 (2019) . - pp. 8814-8818.
ISSN 1523-7052
DOI: https://doi.org/10.1021/acs.orglett.9b03453

Abstract in another language

Cyclopropanation reactions of carbenes with arenes provide a straightforward pathway to norcaradienes or cycloheptatrienes. This reaction normally requires harsh reaction conditions or transition-metal catalysts. In this report, we describe the metal-free visible-light photolysis of aryl diazoacetates in aromatic solvents, which provides access to the norcaradiene ring system in a highly regio- and stereoselective manner. The mild reaction conditions of this approach also allow chemoselective cyclopropanation of substituted arenes without competing C–H functionalization reactions.

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 II - Bioorganic Chemistry > Chair Organic Chemistry II - Bioorganic Chemistry - Univ.-Prof. Dr. René M. Koenigs
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 02 Apr 2025 11:29
Last Modified: 14 May 2025 07:54
URI: https://eref.uni-bayreuth.de/id/eprint/93155