化学
分子内力
烯丙基重排
接受者
组合化学
功能群
激进的
光化学
电子供体
分子
电子转移
氢原子
光诱导电子转移
有机合成
电子受体
有机化学
催化作用
群(周期表)
物理
凝聚态物理
聚合物
作者
Jianzhong Lu,Kaiyao Yuan,Jia-Lian Zheng,He Zhang,Shuting Chen,Ji Ma,Бо Лю,Binbin Tu,Guozhu Zhang,R.T. Guo
标识
DOI:10.1002/anie.202409310
摘要
Allylic amines are prevalent and vital structural components present in many bioactive compounds and natural products. Additionally, they serve as valuable intermediates and building blocks, with wide‐ranging applications in organic synthesis. However, direct α‐C(sp3)‐H alkenylation of feedstock amines, particularly for the preparation of α‐alkenylated cyclic amines, has posed a longstanding challenge. Herein, we present a general, mild, operationally simple, and transition‐metal‐free α‐alkenylation of various readily available amines with alkenylborate esters in excellent E/Z ‐ and diastereoselectivities. This method features good compatibility with water and oxygen, broad substrate scope, and excellent functional group tolerance, thereby enabling the late‐stage modification of various complex molecules. Mechanistic studies suggest that the formation of a photoactive electron donor‐acceptor complex between 2‐iodobenzamide and the tetraalkoxyborate anion, which subsequently undergoes photoinduced single electron transfer and intramolecular 1,5‐hydrogen atom transfer to generate the crucial α‐amino radicals, is the key to success of this chemistry.
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