The first and efficient synthesis of some of the polyhalogenated benzobarrelenes: unusual formation of a benzosemibullvalene derivative

A novel synthetic route based on [4+2] cycloaddition for dibromobenzobarrelene derivatives starting from in situ generated 3,5‐dibromo‐1,2‐didehydrobenzene and mesitylene, 1,2,4,5‐tetramethylbenzene, 1,2,3,5‐tetramethylbenzene, pentamethylbenzene, 1,3‐dimethoxybenzene, and 2,4,6‐trimethylbromobenzene, respectively, was developed. Thus, six novel dibromobenzobarrelenes with diverse substitution patterns at the barrelene framework including chiral derivatives are reported. The benzobarrelene 6,8‐dibromo‐1,3,10‐trimethyl‐1,4‐dihydro‐1,4‐ethenonaphthalene (1a) was functionalized at the annulated benzene ring to give three novel carboxylic acids and two novel phosphonic acid esters. Selected benzobarrelene complexes with RhICl were tested for their catalytic activity in the 1,4‐addition of phenylboronic acid towards cyclohex‐2‐enone. Turnover frequencies up to 3405 h–1 were observed, which are among the highest reported so far for Rh–diene complexes in this type of C–C coupling reaction.

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The first and efficient synthesis of some of the polyhalogenated benzobarrelenes: unusual formation of a benzosemibullvalene derivative

Cited by 8 publications

References 40 publications

Intramolecular Benzyne–Phenolate [4+2] Cycloadditions

Intramolecular Benzyne–Phenolate [4+2] Cycloadditions

Intramolecular Benzyne–Phenolate [4+2] Cycloadditions

Synthesis of Dibromobenzobarrelene Derivatives and Catalytic Activity of Their Rhodium Complexes

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