6533b854fe1ef96bd12adf5a

RESEARCH PRODUCT

Ir-Catalyzed Cycloaddition of Tribenzocyclyne with Biphenylenes

Monika StaśLubomír RulíšekJaroslav JackoMartin KotoraIvana Císařová

subject

Reaction conditionschemistry.chemical_classificationDouble bondchemistryBergman cyclizationOrganic ChemistrySide productHydrogen transferAnnuleneMedicinal chemistryCycloadditionCatalysis

description

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.

yearjournalcountryeditionlanguage
2021-09-17Journal of Organic Chemistry
10.1021/acs.joc.1c01118https://doi.org/10.1021/acs.joc.1c01118