Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency
Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions has already been demonstrated to be effective in providing alternative routes for cross-coupling as w...
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| Published in | Chemical Society reviews Vol. 51; no. 6; pp. 2313 - 2382 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
21.03.2022
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| Subjects | |
| Online Access | Get full text |
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| Abstract | Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions has already been demonstrated to be effective in providing alternative routes for cross-coupling as well as multicomponent reactions. The photocatalyst allows the generation of high-energy intermediates through light irradiation rather than using highly reactive reagents or harsh reaction conditions. In a similar vein, organic electrochemistry has experienced a fruitful renaissance as a tool for generating reactive intermediates without the need for any catalyst. Such milder approaches pose the basis toward higher selectivity and broader applicability. In photocatalyzed and electrochemical multicomponent reactions, the generation of the radical species acts as a starter of the cascade of events. This allows for diverse reactivity and the use of reagents is usually not covered by classical methods. Owing to the availability of cheaper and more standardized photo- and electrochemical reactors, as well as easily scalable flow-setups, it is not surprising that these two fields have become areas of increased research interest. Keeping these in view, this review is aimed at providing an overview of the synthetic approaches in the design of MCRs involving photoredox catalysis and/or electrochemical activation as a crucial step with particular focus on the choice of the difunctionalized reagent.
This review offers an overview of recent synthetic strategies employing photoredox catalysis and electrochemistry in the framework of multicomponent reactions. |
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| AbstractList | Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions has already been demonstrated to be effective in providing alternative routes for cross-coupling as well as multicomponent reactions. The photocatalyst allows the generation of high-energy intermediates through light irradiation rather than using highly reactive reagents or harsh reaction conditions. In a similar vein, organic electrochemistry has experienced a fruitful renaissance as a tool for generating reactive intermediates without the need for any catalyst. Such milder approaches pose the basis toward higher selectivity and broader applicability. In photocatalyzed and electrochemical multicomponent reactions, the generation of the radical species acts as a starter of the cascade of events. This allows for diverse reactivity and the use of reagents is usually not covered by classical methods. Owing to the availability of cheaper and more standardized photo- and electrochemical reactors, as well as easily scalable flow-setups, it is not surprising that these two fields have become areas of increased research interest. Keeping these in view, this review is aimed at providing an overview of the synthetic approaches in the design of MCRs involving photoredox catalysis and/or electrochemical activation as a crucial step with particular focus on the choice of the difunctionalized reagent. Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions has already been demonstrated to be effective in providing alternative routes for cross-coupling as well as multicomponent reactions. The photocatalyst allows the generation of high-energy intermediates through light irradiation rather than using highly reactive reagents or harsh reaction conditions. In a similar vein, organic electrochemistry has experienced a fruitful renaissance as a tool for generating reactive intermediates without the need for any catalyst. Such milder approaches pose the basis toward higher selectivity and broader applicability. In photocatalyzed and electrochemical multicomponent reactions, the generation of the radical species acts as a starter of the cascade of events. This allows for diverse reactivity and the use of reagents is usually not covered by classical methods. Owing to the availability of cheaper and more standardized photo- and electrochemical reactors, as well as easily scalable flow-setups, it is not surprising that these two fields have become areas of increased research interest. Keeping these in view, this review is aimed at providing an overview of the synthetic approaches in the design of MCRs involving photoredox catalysis and/or electrochemical activation as a crucial step with particular focus on the choice of the difunctionalized reagent. This review offers an overview of recent synthetic strategies employing photoredox catalysis and electrochemistry in the framework of multicomponent reactions. Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions has already been demonstrated to be effective in providing alternative routes for cross-coupling as well as multicomponent reactions. The photocatalyst allows the generation of high-energy intermediates through light irradiation rather than using highly reactive reagents or harsh reaction conditions. In a similar vein, organic electrochemistry has experienced a fruitful renaissance as a tool for generating reactive intermediates without the need for any catalyst. Such milder approaches pose the basis toward higher selectivity and broader applicability. In photocatalyzed and electrochemical multicomponent reactions, the generation of the radical species acts as a starter of the cascade of events. This allows for diverse reactivity and the use of reagents is usually not covered by classical methods. Owing to the availability of cheaper and more standardized photo- and electrochemical reactors, as well as easily scalable flow-setups, it is not surprising that these two fields have become areas of increased research interest. Keeping these in view, this review is aimed at providing an overview of the synthetic approaches in the design of MCRs involving photoredox catalysis and/or electrochemical activation as a crucial step with particular focus on the choice of the difunctionalized reagent.Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions has already been demonstrated to be effective in providing alternative routes for cross-coupling as well as multicomponent reactions. The photocatalyst allows the generation of high-energy intermediates through light irradiation rather than using highly reactive reagents or harsh reaction conditions. In a similar vein, organic electrochemistry has experienced a fruitful renaissance as a tool for generating reactive intermediates without the need for any catalyst. Such milder approaches pose the basis toward higher selectivity and broader applicability. In photocatalyzed and electrochemical multicomponent reactions, the generation of the radical species acts as a starter of the cascade of events. This allows for diverse reactivity and the use of reagents is usually not covered by classical methods. Owing to the availability of cheaper and more standardized photo- and electrochemical reactors, as well as easily scalable flow-setups, it is not surprising that these two fields have become areas of increased research interest. Keeping these in view, this review is aimed at providing an overview of the synthetic approaches in the design of MCRs involving photoredox catalysis and/or electrochemical activation as a crucial step with particular focus on the choice of the difunctionalized reagent. |
| Author | You, Shu-Li Coppola, Guglielmo A Sharma, Upendra K Pillitteri, Serena Van der Eycken, Erik V |
| AuthorAffiliation | State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences Peoples' Friendship University of Russia (RUDN University) Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven) |
| AuthorAffiliation_xml | – name: Peoples' Friendship University of Russia (RUDN University) – name: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences – name: Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven) |
| Author_xml | – sequence: 1 givenname: Guglielmo A surname: Coppola fullname: Coppola, Guglielmo A – sequence: 2 givenname: Serena surname: Pillitteri fullname: Pillitteri, Serena – sequence: 3 givenname: Erik V surname: Van der Eycken fullname: Van der Eycken, Erik V – sequence: 4 givenname: Shu-Li surname: You fullname: You, Shu-Li – sequence: 5 givenname: Upendra K surname: Sharma fullname: Sharma, Upendra K |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/35244107$$D View this record in MEDLINE/PubMed |
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| Notes | Serena Pillitteri received her Master's degree with summa cum laude in Pharmaceutical Chemistry and Technology at the University of Turin (Italy) in 2019. Her undergraduate thesis focused on novel approaches for the generation of C-based radicals from boronic acid derivatives under photocatalyzed conditions and was conducted under the guidance of Prof. Erik Van der Eycken and Dr Upendra K. Sharma at KU Leuven (Belgium). After her master thesis, she started her PhD in the same group as an FWO researcher. Her research interests focus on the application of visible-light photoredox catalysis in continuous flow and on the development of novel synthetic methodologies for the generation of C-based radicals. Shu-Li You received his BSc in Chemistry from Nankai University (1996). He then obtained his PhD from the Shanghai Institute of Organic Chemistry (SIOC) in 2001 under the supervision of Prof. Lixin Dai before doing postdoctoral studies with Prof. Jeffery Kelly at The Scripps Research Institute. From 2004, he worked at the Genomics Institute of the Novartis Research Foundation as a PI before returning to SIOC as a Professor in 2006. His research interests mainly focus on asymmetric C-H functionalization and catalytic asymmetric dearomatization (CADA) reactions. He has published over 300 research papers in international peer-reviewed journals and edited two books. Upendra K. Sharma received his PhD (2011) from CSIR-Institute of Himalayan Bioresource Technology, Palampur, India. Thereafter, he worked as an assistant professor for a short period at the National Institute of Technology, Jalandhar, India. In 2013, he joined the research group of Prof. Erik Van der Eycken at the University of Leuven, Belgium, followed by postdoctoral stints with Prof. Steven Ley (University of Cambridge), Prof. Timothy Noël (University of Eindhoven), and Prof. Shu-Li You (SIOC, China). In 2020, he joined KU Leuven as a senior research-expert. His research interests include new reaction methodologies, photoredox catalysis, C-H functionalizations, and flow chemistry. Guglielmo A. Coppola received his Master's degree in Pharmaceutical Chemistry and Technology (2017) from Sapienza University of Rome. Later in the same year, he joined LOMAC through an Erasmus+ scholarship working on metal-free spirocyclizations. He is currently working as a PhD student under the supervision of Prof. Erik Van der Eycken and Prof. Hans Steenackers at KU Leuven. His research focuses on the synthesis of bioactive heterocycles. Erik V. Van der Eycken is Full Prof. of Organic Chemistry and Head of the Division of Molecular Design & Synthesis at KU Leuven, Belgium. He received his PhD degree (1987) in organic chemistry from the University of Ghent, Belgium. He spent time as a visiting scientist at the University of Graz (2002) with Prof. C. O. Kappe, at The Scripps Research Institute (La Jolla, USA) (2003) in the group of K. B. Sharpless, and at Uppsala University (2004) with Prof. M. Larhed and Prof. A. Hallberg. The main focus of his research is on the development of new synthetic methodologies in combination with enabling techniques. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 ObjectType-Review-3 content type line 23 |
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| Snippet | Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The... |
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| SubjectTerms | Catalysis Chemical reactions Chemical reactors Cross coupling cross-coupling reactions Electrochemical activation Electrochemistry energy efficiency irradiation light Light irradiation Organic chemistry photocatalysis photocatalysts Photoredox catalysis Reagents redox reactions Selectivity |
| Title | Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency |
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