0000000000954321
AUTHOR
Jaroslav Jacko
Ir-Catalyzed Cycloaddition of Tribenzocyclyne with Biphenylenes
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.
CCDC 2074639: Experimental Crystal Structure Determination
Related Article: Jaroslav Jacko, Monika Staś, Lubomír Rulíšek, Ivana Císařová, Martin Kotora|2022|J.Org.Chem.|87|744|doi:10.1021/acs.joc.1c01118
CCDC 2074638: Experimental Crystal Structure Determination
Related Article: Jaroslav Jacko, Monika Staś, Lubomír Rulíšek, Ivana Císařová, Martin Kotora|2022|J.Org.Chem.|87|744|doi:10.1021/acs.joc.1c01118
CCDC 2074634: Experimental Crystal Structure Determination
Related Article: Jaroslav Jacko, Monika Staś, Lubomír Rulíšek, Ivana Císařová, Martin Kotora|2022|J.Org.Chem.|87|744|doi:10.1021/acs.joc.1c01118
CCDC 2074637: Experimental Crystal Structure Determination
Related Article: Jaroslav Jacko, Monika Staś, Lubomír Rulíšek, Ivana Císařová, Martin Kotora|2022|J.Org.Chem.|87|744|doi:10.1021/acs.joc.1c01118
CCDC 2074635: Experimental Crystal Structure Determination
Related Article: Jaroslav Jacko, Monika Staś, Lubomír Rulíšek, Ivana Císařová, Martin Kotora|2022|J.Org.Chem.|87|744|doi:10.1021/acs.joc.1c01118
CCDC 2074640: Experimental Crystal Structure Determination
Related Article: Jaroslav Jacko, Monika Staś, Lubomír Rulíšek, Ivana Císařová, Martin Kotora|2022|J.Org.Chem.|87|744|doi:10.1021/acs.joc.1c01118
CCDC 2074636: Experimental Crystal Structure Determination
Related Article: Jaroslav Jacko, Monika Staś, Lubomír Rulíšek, Ivana Císařová, Martin Kotora|2022|J.Org.Chem.|87|744|doi:10.1021/acs.joc.1c01118