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Divergent Electrochemical Synthesis of Indoles through pKa Regulation of Amides: Synthetic and Mechanistic Insights
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2024-01-30 , DOI: 10.1002/chem.202304002
Samrat Mallick 1 , Tanumoy Mandal 1 , Nidhi Kumari 1 , Lisa Roy 2 , Suman De Sarkar 1
Affiliation  

This manuscript describes an unprecedented chemo-divergent synthesis of C-3-free and C-3-selenylated indoles with exclusive chemoselectivity through controlled and selective electrochemical oxidation of 2-amino stilbene derivatives. The chemoselectivity was achieved by regulating the pKa of the N−H proton. Detailed experimental and computational studies assist in explaining the ambiguous chemical nature of diversely N-protected 2-amino stilbenes in synthesizing chemo-divergent indole frameworks.

中文翻译:


通过酰胺的 pKa 调节进行吲哚的不同电化学合成:合成和机理见解



该手稿描述了通过 2-氨基二苯乙烯衍生物的受控和选择性电化学氧化,以独特的化学选择性合成无 C-3 和 C-3-硒化吲哚的前所未有的化学发散合成。化学选择性是通过调节 NH质子pKa来实现的。详细的实验和计算研究有助于解释不同N保护的 2-氨基二苯乙烯在合成化学分歧吲哚框架中的模糊化学性质。
更新日期:2024-01-30
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