Metal- and Reagent-Free Dehydrogenative Formal Benzyl-Aryl Cross-Coupling by Anodic Activation in 1,1,1,3,3,3-Hexafluoropropan-2-ol
Metal- and Reagent-Free Dehydrogenative Formal Benzyl-Aryl Cross-Coupling by Anodic Activation in 1,1,1,3,3,3-Hexafluoropropan-2-ol
复制标题
DOI：
10.1002/anie.201804997
复制
发表时间：
2018-09-10
影响因子：
16.6
通讯作者：
Waldvogel, Siegfried R.
中科院分区：
文献类型：
--
作者：
Imada, Yasushi;Roeckl, Johannes L.;Waldvogel, Siegfried R.
已经开发出一种使用 1,1,1,3,3,3-六氟丙-2-醇 (HFIP) 的苄位选择性脱氢电化学功能化。电生成的产物是用于后续功能化的多功能中间体，因为它们充当易于激活的掩蔽苄基阳离子。在此，我们报告了一种可持续的、可扩展的、无试剂和金属的脱氢形式苄基芳基交叉偶联。通过使用酸来释放苄基阳离子。在芳香族亲核试剂存在下可以获得有价值的二芳基甲烷。由于氧化剂被电子取代，直接使用电可以实现安全且环保的化学转化。可以使用多种不同的底物和亲核试剂。
A selective dehydrogenative electrochemical functionalization of benzylic positions that employs 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) has been developed. The electrogenerated products are versatile intermediates for subsequent functionalizations as they act as masked benzylic cations that can be easily activated. Herein, we report a sustainable, scalable, and reagent- and metal-free dehydrogenative formal benzyl-aryl cross-coupling. Liberation of the benzylic cation was accomplished through the use of acid. Valuable diarylmethanes are accessible in the presence of aromatic nucleophiles. The direct application of electricity enables a safe and environmentally benign chemical transformation as oxidizers are replaced by electrons. A broad variety of different substrates and nucleophiles can be employed.