Temperature-Controlled Photoreactors and ChemBeads as Key Technologies for Robust and Practical Photochemical HTE,Organic Process Research & Development

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Temperature-Controlled Photoreactors and ChemBeads as Key Technologies for Robust and Practical Photochemical HTE
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2023-04-13 , DOI: 10.1021/acs.oprd.3c00061
Paolo Piacentini ₁ , James M. Fordham ₁ , Eloisa Serrano ₁ , Luca Hepp ₁ , Marco Santagostino ₁

Affiliation

We report on our successful efforts to advance the robustness of screening photochemical reactions run in batch by using commercially available, temperature-controlled multiwell reactors in combination with ChemBead technology for precise solid dosing of the photoredox catalysts. The utility of this experimental setup was validated for five reaction classes, which were selected based on their varying sensitivity toward oxygen, temperature, and degree of homogeneity. The advantages and potential issues associated with the use of ChemBeads in high-throughput experimentation (HTE) photochemistry have been critically assessed. The presented multiarray photochemical setup was then applied to improve the scope of an Ir/Ni-co-catalyzed C–N visible-light cross-coupling reaction between aryl halides and fluorinated amines, which had remained limited until now. The optimal combination of categorical variables, the functional group compatibility, and the required structural elements in both the nucleophile and the electrophile partner for successful reactions were pinpointed. The reproducibility and transferability of the results to a larger-scale batch platform (PHIL photoreactor) was confirmed with a scale-up factor of 100. Finally, some suggestions for further improvements for temperature-controlled multiwell photoreactors compatible with HTE setups were listed.

中文翻译：

温控光反应器和 ChemBeads 作为稳健实用光化学 HTE 的关键技术

我们报告了我们通过使用市售的温控多孔反应器并结合 ChemBead 技术来提高批量运行的筛选光化学反应的稳健性的成功努力，以实现光氧化还原催化剂的精确固体剂量。该实验装置的效用针对五个反应类别进行了验证，这些反应类别是根据它们对氧气、温度和均匀度的不同敏感性而选择的。与在高通量实验 (HTE) 光化学中使用 ChemBeads 相关的优势和潜在问题已得到严格评估。然后应用所提出的多阵列光化学装置来改善芳基卤化物和氟化胺之间 Ir/Ni 共催化的 C-N 可见光交叉偶联反应的范围，直到现在仍然是有限的。明确了分类变量的最佳组合、官能团相容性以及成功反应所需的亲核试剂和亲电试剂伙伴中的结构元素。将结果的重现性和可转移性确认为更大规模的批处理平台（PHIL 光反应器），放大系数为 100。最后，列出了进一步改进与 HTE 设置兼容的温控多孔光反应器的一些建议。

更新日期：2023-04-13

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