Small molecules containing cyclopropane–heteroatom linkages are commonly needed in medicinal chemistry campaigns yet are problematic to prepare using existing methods. To address this issue, a scalable Chan–Lam cyclopropylation reaction using potassium cyclopropyl trifluoroborate has been developed. With phenol nucleophiles, the reaction effects O-cyclopropylation, whereas with 2-pyridones, 2-hydroxybenzimidazoles, and 2-aminopyridines the reaction brings about N-cyclopropylation. The transformation is catalyzed by Cu(OAc)₂ and 1,10-phenanthroline and employs 1 atm of O₂ as the terminal oxidant. This method is operationally convenient to perform and provides a simple, strategic disconnection toward the synthesis of cyclopropyl aryl ethers and cyclopropyl amine derivatives bearing an array of functional groups.

中文翻译：

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铜催化苯酚和氮杂杂环的Chan–Lam环丙基化

在药物化学研究中通常需要含有环丙烷-杂原子键的小分子，但使用现有方法制备时会遇到问题。为了解决这个问题，已经开发了使用环丙基三氟硼酸钾的可扩展Chan-Lam环丙基化反应。对于酚亲核试剂，该反应实现O-环丙基化，而对于2-吡啶酮，2-羟基苯并咪唑和2-氨基吡啶，该反应引起N-环丙基化。该转化由Cu（OAc）₂和1,10-菲咯啉催化，并使用1 atm的O ₂作为末端氧化剂。该方法在操作上易于操作，并且为合成带有一系列官能团的环丙基芳基醚和环丙基胺衍生物提供了简单，战略上的连接。