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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
C(sp3)-H functionalization of N-protected dialkylpyrrole derivatives with azodicarboxylates
Jing Guo1, Maying Yan1, Lei Xiao1
1Institute of Drug Discovery Technology and Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo 315211, Zhejiang, China. guojing@nbu.edu.cn.
Abstract:
A metal-free, catalytic route to the activation of C(sp3)-H bonds in N-protected dialkylpyrroles to diazodicarboxylates is reported using HB(C6F5)2 as the optimized catalyst. These reactions tolerate aryl and alkyl substituents on the pyrrole N-atom as well as variation in the azodicarboxylates giving rise to 41 examples. These reactions were also performed on a gram scale and conversion to the corresponding amino-esters is demonstrated. A DFT computation study reveals that the Lewis acid adduct of azodicarboxylates generates a Lewis acidic N-atom capable of hydride abstraction from dimethylpyrrole, ultimately effecting C(sp3)-H functionalization.
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