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Electrochemical Cross-Dehydrogenative Coupling between Phenols and β-Dicarbonyl Compounds: Facile Construction of Benzofurans.
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-01-03 , DOI: 10.1002/chem.201904750
Yandong Wang 1 , Bailin Tian 2 , Mengning Ding 2 , Zhuangzhi Shi 1
Affiliation  

Preparative electrochemical synthesis is an ideal method for establishing green, sustainable processes. The major benefits of electro-organic strategy over conventional chemical synthesis are the avoidance of reagent waste and the mild reaction conditions. Here, an intermolecular cross-dehydrogenative coupling (CDC) between phenols and β-dicarbonyl compounds to build various benzofurans under undivided electrolytic conditions has been developed. Neither transition metals nor external chemical oxidants are required to facilitate the dehydrogenation and dehydration processes. The key factor in the success was the use of n Bu 4 NBF 4 as the electrolyte and hexafluoroisopropanol (HFIP) as the solvent, which play key roles in the cyclocondensation step. This electrolysis is scalable and can be used as a key step in drug synthesis. On the basis of the several experimental results, the mechanism, particularly of the remarkable anodic oxidation and cyclization process, was illustrated.

中文翻译:

苯酚和β-二羰基化合物之间的电化学交叉脱氢偶联:苯并呋喃的简便构建。

制备电化学合成是建立绿色可持续工艺的理想方法。与传统的化学合成方法相比,有机化学策略的主要优点是避免了试剂浪费和温和的反应条件。在此,已经开发了在不分开的电解条件下,酚与β-二羰基化合物之间的分子间交叉脱氢偶联(CDC),以构建各种苯并呋喃。过渡金属或外部化学氧化剂都不需要以促进脱氢和脱水过程。成功的关键因素是使用n Bu 4 NBF 4作为电解质,使用六氟异丙醇(HFIP)作为溶剂,它们在环缩合步骤中起关键作用。这种电解是可扩展的,可以用作药物合成中的关键步骤。
更新日期:2020-03-09
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