The Birch reduction dearomatizes arenes into 1,4-cyclohexadienes. Despite substantial efforts devoted to avoiding ammonia and cryogenic conditions, the traditional, cumbersome, and dangerous procedure remains the standard. The Benkeser reduction with lithium in ethylenediamine converts arenes to a mixture of cyclohexenes and cyclohexanes; this is operationally easier than the Birch reduction but does not afford 1,4-cyclohexadienes. Here, we report a Birch reduction promoted by lithium and ethylenediamine (or analogs) in tetrahydrofuran at ambient temperature. Our method is easy to set up, inexpensive, scalable, rapid, accessible to any chemical laboratory, and capable of reducing both electron-rich and electron-deficient substrates. Our protocol is also compatible with organocuprate chemistry for further functionalization.

中文翻译：

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在四氢呋喃中用锂和乙二胺进行可扩展的 Birch 还原

Birch 还原将芳烃脱芳构化为 1,4-环己二烯。尽管为避免氨和低温条件付出了巨大努力，但传统、繁琐且危险的程序仍然是标准。Benkeser 用乙二胺中的锂还原将芳烃转化为环己烯和环己烷的混合物；这在操作上比 Birch 还原更容易，但不能提供 1,4-环己二烯。在这里，我们报告了锂和乙二胺（或类似物）在环境温度下在四氢呋喃中促进的 Birch 还原。我们的方法易于设置、价格低廉、可扩展、快速、可供任何化学实验室使用，并且能够减少富电子和缺电子底物。我们的协议还与有机铜酸盐化学兼容，以进行进一步的功能化。