Journal of Organic Chemistry p. 2082 - 2091 (2020)
Update date:2022-09-26
Topics:
Ishida, Kosuke
Kawanishi, Tatsuya
Kayahara, Eiichi
Yamago, Shigeru
Selective and large-scale synthesis of [8]cycloparaphenylene (CPP) was achieved in seven steps starting from commercially available 4-bromo-4′-hydroxybiphenyl and 4,4′-dibromobiphenyl. The key unsymmetrical tetraring unit, 4-bromophenyl and 4′-bromobiphenyl-substituted cis-1,4-bis(triethylsiloxy)-2,5-cyclohexadiene-1,4-diyl (5fA), was synthesized on an ~50 g scale by stereoselective cis-addition of 4-bromo-4′-lithiobiphenyl to 4-(4-bromophenyl)-4-hydroxy-2,5-cyclohexadien-1-one, which was synthesized on an ~100 g scale. Platinum-mediated selective dimerization of the four-ring unit 5fB and subsequent reductive aromatization of the cyclohexadiene-diyl by H2SnCl4 gave 2 g of [8]CPP in 6.6% overall yield (10.2% on small scale).
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