4.7 Article

Ir-Catalyzed Cycloaddition of Tribenzocyclyne with Biphenylenes

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JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 1, 页码 744-750

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01118

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  1. Czech Science Foundation [21-29124S]

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We have demonstrated that C-C bond activation in biphenylenes catalyzed by iridium, followed by reaction with tribenzocyclyne, is a suitable method for synthesizing strained and unknown monoadducts. By modifying the reaction conditions, [12]annulene products with cis and/or trans double bonds formed by hydrogen transfer can also be obtained. In addition, a [9]annulene side product was formed during the reaction.
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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