C(sp)-H functionalization in non-aromatic azomethine-based heterocycles
Direct C(sp 2 )-H functionalization of the endocyclic azomethine and aldonitrone moieties in non-aromatic azaheterocycles has established itself as a promising methodology over the last decade. Transition metal-catalyzed cross-coupling reactions, α-metalation-electrophile quenching protocols, and (m...
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| Published in | Organic & biomolecular chemistry Vol. 19; no. 2; pp. 297 - 312 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
21.01.2021
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| Subjects | |
| Online Access | Get full text |
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| Summary: | Direct C(sp
2
)-H functionalization of the endocyclic azomethine and aldonitrone moieties in non-aromatic azaheterocycles has established itself as a promising methodology over the last decade. Transition metal-catalyzed cross-coupling reactions, α-metalation-electrophile quenching protocols, and (metal-free) nucleophilic substitution of hydrogen reactions (S
N
H
) are the major routes applied on cyclic imines and their derivatives. In this overview, we show the tangible progress made in this area during the period from 2008 to 2020.
This review highlights the advances in the direct C(sp
2
)-H functionalization of cyclic aldimines, aldohydrazones, and aldonitrones since 2008. |
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| Bibliography: | SynOpen CASCH. He is an editor of Advances in Heterocyclic Chemistry Mikhail V. Varaksin graduated from the Ural State Technical University in 2008. In 2010, he earned his PhD in Organic Chemistry. In 2011, he joined the Department of Organic & Biomolecular Chemistry at Ural Federal University as an Associate Professor. His current research interests include the development of novel pot, atom, and step economical approaches based on the methodology of C-H bond functionalization in both (hetero)aromatic and non-aromatic substrates in the design of novel heterocyclic derivatives of nitroxide radicals, calixarenes, carboranes, and also advanced materials for molecular electronics. Bert U. W. Maes obtained his PhD in Organic Chemistry at UAntwerp and subsequently received a Post-Doctoral Fellowship of the Science Foundation (FWO-Flanders) in Belgium. He worked at the École Normale Supérieure in Paris (mechanisms in catalysis) with Prof. Anny Jutand (CNRS). Bert Maes was appointed Assistant Professor (Docent) in the Department of Chemistry at UAntwerp in 2003 and currently holds a Full Professorship (Gewoon Hoogleraar) of Organic Chemistry at UAntwerp; since 2009 he has been a Research Professor. In 2019 he was appointed as Collen-Francqui Research Professor by the Francqui Foundation. In 2015-2016 he acted as chairman of the Department of Chemistry. His research interests cover the fields of heterocyclic chemistry, organometallic chemistry and homogeneous catalysis with a special focus on the development of sustainable synthetic methodology. The research in his group involves base metal catalysis, aerobic oxidation, strong bond activation, renewables, and green metrics analysis. His research group partakes in one of the Excellence Centers of UAntwerp and an editorial board member of Topics in Heterocyclic Chemistry . Alexey A. Akulov obtained his MSc degree in Chemistry at Ural Federal University in 2020. In 2016, he joined the Department of Organic & Biomolecular Chemistry at the same university, where he is currently working as a research engineer. His scientific activities are focused on the C-H functionalization methodology development with regard to azaheterocyclic compounds and, in particular, on the elaboration of both novel transition metal-catalyzed and metal-free cross-dehydrogenative coupling approaches. Pieter Mampuys obtained his PhD in Organic Chemistry from UAntwerpen and the Vrije Universiteit Amsterdam under the supervision of Profs Bert Maes and Romano Orru in 2017. He also worked at Likat in Germany with Prof. Matthias Beller. In 2018, he was appointed as a post-doctoral researcher at UAntwerpen. His second post-doc is in collaboration with the company Covestro. His current research interests include base metal-catalyzed multicomponent chemistry, organometallics, sulfur chemisty, photoredox catalysis and green metrics analysis. and Valery N. Charushin is a full member of the Russian Academy of Sciences (RAS), Professor at the Department of Organic and Biomolecular Chemistry at Ural Federal University, and Head of Postovsky Institute of Organic Synthesis of the Ural Branch of RAS. Prof. Charushin graduated with honors from Ural Polytechnical Institute in 1973. In 1976, he earned his PhD in Organic Chemistry. In 1981-1982, he joined the research group of Prof. Henk van der Plas (Wageningen University, Wageningen, Netherlands), where he was working on the ring transformations of azines. In 1987, he received a Doctor of Science degree in Organic Chemistry. His current research interests include novel methods in organic synthesis, heterocyclic and medicinal chemistry. i.e. Oleg N. Chupakhin is a full member of the Russian Academy of Sciences, Professor and ex-Head of the Department of Organic & Biomolecular Chemistry at Ural Federal University, and Chief Researcher at Postovsky Institute of Organic Synthesis of Ural Branch of RAS. Prof. Chupakhin graduated with honors from Ural Polytechnical Institute in 1957. He earned his PhD in Organic Chemistry in 1962 and Doctor of Science degree in 1976. Current research interests: new methodologies in organic synthesis, structural analysis of organic compounds, mechanisms of organic reactions, heterocyclic chemistry, green chemistry, industrial chemistry, environmental chemistry, medicinal chemistry, chemosensors, molecular recognition and supramolecular chemistry. ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-3 content type line 23 ObjectType-Review-1 |
| ISSN: | 1477-0520 1477-0539 |
| DOI: | 10.1039/d0ob01580f |