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Iodide anion enables a reductive cross‐electrophile coupling for preparing tertiary amines
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2024-11-19 , DOI: 10.1002/anie.202409688 Miran Lemmerer, Veronica Tona, David Just, Miloš Vavrík, Boris Maryasin, Giovanni Di Mauro, Andreas B. zur Bonsen, Daniel Kaiser, Nuno Maulide
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2024-11-19 , DOI: 10.1002/anie.202409688 Miran Lemmerer, Veronica Tona, David Just, Miloš Vavrík, Boris Maryasin, Giovanni Di Mauro, Andreas B. zur Bonsen, Daniel Kaiser, Nuno Maulide
The reducing power of iodide anion is an underexplored property that can be used for the cross‐electrophile coupling of organic molecules. Herein we harness this trait for the preparation of tertiary amines through the combination of two simple reagents: an electrophilic‐carbon precursor and an iminium iodide in a dual role—both as nitrogen‐containing building block and as reducing agent. The underlying mechanism of this new C–C bond‐formation paradigm is explored through a combination of experiment and quantum chemical calculations.
中文翻译:
碘化物阴离子可实现还原叉亲电偶联,用于制备叔胺
碘化物阴离子的还原能力是一种未被充分开发的特性,可用于有机分子的交叉亲电偶联。在本文中,我们通过组合两种简单的试剂来利用这一特性来制备叔胺:亲电碳前驱体和具有双重作用的碘化亚胺——既作为含氮结构单元,也作为还原剂。通过实验和量子化学计算的结合来探索这种新的 C-C 键形成范式的潜在机制。
更新日期:2024-11-19
中文翻译:
碘化物阴离子可实现还原叉亲电偶联,用于制备叔胺
碘化物阴离子的还原能力是一种未被充分开发的特性,可用于有机分子的交叉亲电偶联。在本文中,我们通过组合两种简单的试剂来利用这一特性来制备叔胺:亲电碳前驱体和具有双重作用的碘化亚胺——既作为含氮结构单元,也作为还原剂。通过实验和量子化学计算的结合来探索这种新的 C-C 键形成范式的潜在机制。