Ir-Catalyzed Cycloaddition of Tribenzocyclyne with Biphenylenes

0551226 - ÚOCHB 2023 RIV US eng J - Journal Article
Jacko, J. - Staś, Monika - Rulíšek, Lubomír - Císařová, I. - Kotora, M.
Ir-Catalyzed Cycloaddition of Tribenzocyclyne with Biphenylenes.
Journal of Organic Chemistry. Roč. 87, č. 1 (2022), s. 744-750. ISSN 0022-3263. E-ISSN 1520-6904
Institutional support: RVO:61388963
Keywords : lithium induced cyclization * C bond cleavage * crystal structure
OECD category: Organic chemistry
Impact factor: 3.6, year: 2022
Method of publishing: Limited access
https://doi.org/10.1021/acs.joc.1c01118

We demonstrate that Ir-catalyzed C–C bond activation in biphenylenes followed by a reaction with tribenzocyclyne is a suitable method for synthesizing strained and unknown monoadducts with the tetradehydrotetrabenzo[a,c,e,i]cyclododecene scaffold ([12]annulenes). Modification of reaction conditions also furnished [12]annulene products with cis and/or trans double bonds formed by hydrogen transfer. The [9]annulene side product was formed upon the reaction of the benzyl radical with tribenzocyclyne during the Bergman cyclization. All isolated compounds were fully characterized by HRMS, NMR, and X-ray diffraction analysis.
Permanent Link: http://hdl.handle.net/11104/0326675


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