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Selective and Gram-Scale Synthesis of [8]Cycloparaphenylene.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-01-31 , DOI: 10.1021/acs.joc.9b02844
Tatsuya Kawanishi 1 , Kosuke Ishida 2 , Eiichi Kayahara 2 , Shigeru Yamago 2
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-01-31 , DOI: 10.1021/acs.joc.9b02844
Tatsuya Kawanishi 1 , Kosuke Ishida 2 , Eiichi Kayahara 2 , Shigeru Yamago 2
Affiliation
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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).
中文翻译:
[8]环对亚苯基的选择性和克级合成。
从商业上可获得的4-溴-4'-羟基联苯和4,4'-二溴联苯开始,分七个步骤实现了[8]环对亚苯基(CPP)的选择性和大规模合成。以〜50 g的规模合成了关键的不对称四环单元4-溴苯基和4'-溴联苯取代的顺1,4-双(三乙基甲硅烷氧基)-2,5-环己二烯-1,4-二基(5fA)通过将4-溴-4'-硫代联苯立体选择性顺式加成到4-(4-溴苯基)-4-羟基-2,5-环己二烯-1-酮上,该合成量约为100 g。铂介导的四环单元5fB的选择性二聚和随后的H2SnCl4还原环己二烯二基的芳构化反应,可得到2 g [8] CPP,总产率为6.6%(小规模为10.2%)。
更新日期:2020-02-03
中文翻译:
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[8]环对亚苯基的选择性和克级合成。
从商业上可获得的4-溴-4'-羟基联苯和4,4'-二溴联苯开始,分七个步骤实现了[8]环对亚苯基(CPP)的选择性和大规模合成。以〜50 g的规模合成了关键的不对称四环单元4-溴苯基和4'-溴联苯取代的顺1,4-双(三乙基甲硅烷氧基)-2,5-环己二烯-1,4-二基(5fA)通过将4-溴-4'-硫代联苯立体选择性顺式加成到4-(4-溴苯基)-4-羟基-2,5-环己二烯-1-酮上,该合成量约为100 g。铂介导的四环单元5fB的选择性二聚和随后的H2SnCl4还原环己二烯二基的芳构化反应,可得到2 g [8] CPP,总产率为6.6%(小规模为10.2%)。