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Ir-Catalyzed Cycloaddition of Tribenzocyclyne with Biphenylenes
Jaroslav Jacko1, Monika Staś2, Lubomír Rulíšek2
1Department of Organic Chemistry, Faculty of Science, Charles University, Albertov 6, 128 43 Praha 2, Czech Republic.
Abstract:
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.
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