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Kilogram-Scale Production of Corannulene

机译：公斤级规模的Corannulene生产

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摘要

An efficient entry process for the synthesis of corannulene has been demonstrated on kilogram scale. Compared to the discovery and gram-scale syntheses, the amounts of solvents and reagents per gram of product were greatly reduced. Priority was given to implement the least toxic agents possible. Improvements in the purification of products obviated the need for column chromatography, alleviating four chromatographic operations. A new reduction method for the final step of the synthesis decreased reaction time from 6 to 0.5 days, and avoided the use of 100 equiv of zinc metal. The process now comprises nine steps, each of which runs smoothly at 100-L scale with a charging of 3-12 kg of educt. A total of 1.3 kg corannulene was isolated. This kilogram-scale process reduces material costs by over 2 orders of magnitude compared to that for the published gram-scale syntheses. Key opportunities in the process are identified for farther improvements that should make synthesis on 100-kg scale feasible with a target price for 1 that is suitable for commercial production and engineering application.
机译：在公斤规模上已经证明了用于合成香兰素的有效进入方法。与发现和克级合成相比，每克产品的溶剂和试剂量大大减少。优先考虑使用毒性最小的药物。产品纯化方面的改进消除了对柱色谱法的需要，从而减少了四种色谱操作。合成最后一步的新还原方法将反应时间从6天减少到0.5天，并避免了使用100当量的锌金属。该过程现在包括9个步骤，每个步骤在100-L规模下平稳运行，并装入3-12 kg的离析物。分离出总共1.3kg的香兰素。与已发布的克级合成方法相比，这种千克级工艺可将材料成本降低2个数量级以上。确定了该过程中的关键机会，以进行进一步的改进，使100千克规模的合成可行，目标价格为1（适用于商业生产和工程应用）。

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