Insertion of ammonia into alkenes to build aromatic N-heterocycles

Ammonia is one of the most abundant and simple nitrogen sources with decent stability and reactivity. Direct insertion of ammonia into a carbon skeleton is an ideal approach to building valuable N -heterocycles for extensive applications with unprecedented atom and step economy. Here, we show an ele...

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Bibliographic Details
Published inNature communications Vol. 13; no. 1; p. 425
Main Authors Liu, Shuai, Cheng, Xu
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 20.01.2022
Nature Publishing Group
Nature Portfolio
Subjects
140/131
140/58
639/638/403/934
639/638/549/933
Alkenes
Ammonia
Atom economy
Carbon
Dehydrogenation
Electrochemistry
Heterocyclic compounds
Humanities and Social Sciences
Hydrogen-based energy
Insertion
multidisciplinary
Nitrogen
Nitrogen sources
Oxidants
Oxidation
Oxidizing agents
Pyridines
Quinoline
Science
Science (multidisciplinary)
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Summary:Ammonia is one of the most abundant and simple nitrogen sources with decent stability and reactivity. Direct insertion of ammonia into a carbon skeleton is an ideal approach to building valuable N -heterocycles for extensive applications with unprecedented atom and step economy. Here, we show an electrochemical dehydrogenative method in which ammonia is inserted directly into alkenes to build aromatic N -heterocycles in a single step without the use of any external oxidant. This new approach achieves 98–99.2% atom economy with hydrogen as the only byproduct. Quinoline and pyridine with diverse substitutions are readily available. In this work, electrochemistry was used to drive a 4-electron oxidation reaction that is hard to access by other protocols, providing a parallel pathway to nitrene chemistry. In a tandem transformation that included three distinct electrochemical processes, the insertion of ammonia further showcased the tremendous potential to manipulate heterocycles derived from Hantzsch ester to diazine via pyridine and pyrrole. Aromatic heterocycles containing nitrogen are ubiquitous in biologically relevant small molecules. Here the authors show an unorthodox methodology for their synthesis, by inserting the nitrogen atom into a carbon ring, with ammonia in electrochemical conditions.
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ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-022-28099-w