Photoredox Catalysis for Building C–C Bonds from C(sp2)–H Bonds
Transition metal-catalyzed C–H bond functionalizations have been the focus of intensive research over the last decades for the formation of C–C bonds from unfunctionalized arenes, heteroarenes, alkenes. These direct transformations provide new approaches in synthesis with high atom- and step-economy...
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| Published in | Chemical reviews Vol. 118; no. 16; pp. 7532 - 7585 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
22.08.2018
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| Subjects | |
| Online Access | Get full text |
| ISSN | 0009-2665 1520-6890 1520-6890 |
| DOI | 10.1021/acs.chemrev.8b00077 |
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| Abstract | Transition metal-catalyzed C–H bond functionalizations have been the focus of intensive research over the last decades for the formation of C–C bonds from unfunctionalized arenes, heteroarenes, alkenes. These direct transformations provide new approaches in synthesis with high atom- and step-economy compared to the traditional catalytic cross-coupling reactions. However, such methods still suffer from several limitations including functional group tolerance and the lack of regioselectivity. In addition, they often require harsh reaction conditions and some of them need the use of strong oxidant, in a stoichiometric amount, avoiding these processes to be truly eco-friendly. The use of photoredox catalysis has contributed to a significant expansion of the scope of C(sp2)–H bond functionalizations which include the direct arylations, (perfluoro)alkylations, acylations, and even cyanations. Most of these transformations involve the photochemical induced generation of a radical followed by its regioselective addition to arenes, heteroarenes, or alkenes, leading to the building of a new C(sp2)–C bond. The use of photoredox catalysis plays crucial roles in these reactions promoting electron transfer, enabling the generation of radical species and single electron either oxidation or reduction. Such reactions operating at room temperature allow the building of C–C bonds with high chemo-, regio-, or stereoselectivity. This review surveys the formation of C(sp2)–C bonds initiated by photoredox catalysis which involves a C(sp2)–H bond functionalization step, describes the advantages compared to traditional C(sp2)–H bond functionalizations, and presents mechanistic insights into the role played by the photoredox catalysts. |
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| AbstractList | Transition metal-catalyzed C–H bond functionalizations have been the focus of intensive research over the last decades for the formation of C–C bonds from unfunctionalized arenes, heteroarenes, alkenes. These direct transformations provide new approaches in synthesis with high atom- and step-economy compared to the traditional catalytic cross-coupling reactions. However, such methods still suffer from several limitations including functional group tolerance and the lack of regioselectivity. In addition, they often require harsh reaction conditions and some of them need the use of strong oxidant, in a stoichiometric amount, avoiding these processes to be truly eco-friendly. The use of photoredox catalysis has contributed to a significant expansion of the scope of C(sp2)–H bond functionalizations which include the direct arylations, (perfluoro)alkylations, acylations, and even cyanations. Most of these transformations involve the photochemical induced generation of a radical followed by its regioselective addition to arenes, heteroarenes, or alkenes, leading to the building of a new C(sp2)–C bond. The use of photoredox catalysis plays crucial roles in these reactions promoting electron transfer, enabling the generation of radical species and single electron either oxidation or reduction. Such reactions operating at room temperature allow the building of C–C bonds with high chemo-, regio-, or stereoselectivity. This review surveys the formation of C(sp2)–C bonds initiated by photoredox catalysis which involves a C(sp2)–H bond functionalization step, describes the advantages compared to traditional C(sp2)–H bond functionalizations, and presents mechanistic insights into the role played by the photoredox catalysts. Transition metal-catalyzed C-H bond functionalizations have been the focus of intensive research over the last decades for the formation of C-C bonds from unfunctionalized arenes, heteroarenes, alkenes. These direct transformations provide new approaches in synthesis with high atom- and step-economy compared to the traditional catalytic cross-coupling reactions. However, such methods still suffer from several limitations including functional group tolerance and the lack of regioselectivity. In addition, they often require harsh reaction conditions and some of them need the use of strong oxidant, in a stoichiometric amount, avoiding these processes to be truly eco-friendly. The use of photoredox catalysis has contributed to a significant expansion of the scope of C(sp )-H bond functionalizations which include the direct arylations, (perfluoro)alkylations, acylations, and even cyanations. Most of these transformations involve the photochemical induced generation of a radical followed by its regioselective addition to arenes, heteroarenes, or alkenes, leading to the building of a new C(sp )-C bond. The use of photoredox catalysis plays crucial roles in these reactions promoting electron transfer, enabling the generation of radical species and single electron either oxidation or reduction. Such reactions operating at room temperature allow the building of C-C bonds with high chemo-, regio-, or stereoselectivity. This review surveys the formation of C(sp )-C bonds initiated by photoredox catalysis which involves a C(sp )-H bond functionalization step, describes the advantages compared to traditional C(sp )-H bond functionalizations, and presents mechanistic insights into the role played by the photoredox catalysts. Transition metal-catalyzed C-H bond functionalizations have been the focus of intensive research over the last decades for the formation of C-C bonds from unfunctionalized arenes, heteroarenes, alkenes. These direct transformations provide new approaches in synthesis with high atom- and step-economy compared to the traditional catalytic cross-coupling reactions. However, such methods still suffer from several limitations including functional group tolerance and the lack of regioselectivity. In addition, they often require harsh reaction conditions and some of them need the use of strong oxidant, in a stoichiometric amount, avoiding these processes to be truly eco-friendly. The use of photoredox catalysis has contributed to a significant expansion of the scope of C(sp)-H bond functionalizations which include the direct arylations, (perfluoro)alkylations, acylations, and even cyanations. Most of these transformations involve the photochemical induced generation of a radical followed by its regioselective addition to arenes, heteroarenes, or alkenes, leading to the building of a new C(sp)-C bond. The use of photoredox catalysis plays crucial roles in these reactions promoting electron transfer, enabling the generation of radical species and single electron either oxidation or reduction. Such reactions operating at room temperature allow the building of C-C bonds with high chemo-, regio-, or stereoselectivity. This review surveys the formation of C(sp)-C bonds initiated by photoredox catalysis which involves a C(sp)-H bond functionalization step, describes the advantages compared to traditional C(sp)-H bond functionalizations, and presents mechanistic insights into the role played by the photoredox catalysts. Transition metal-catalyzed C-H bond functionalizations have been the focus of intensive research over the last decades for the formation of C-C bonds from unfunctionalized arenes, heteroarenes, alkenes. These direct transformations provide new approaches in synthesis with high atom- and step-economy compared to the traditional catalytic cross-coupling reactions. However, such methods still suffer from several limitations including functional group tolerance and the lack of regioselectivity. In addition, they often require harsh reaction conditions and some of them need the use of strong oxidant, in a stoichiometric amount, avoiding these processes to be truly eco-friendly. The use of photoredox catalysis has contributed to a significant expansion of the scope of C(sp2)-H bond functionalizations which include the direct arylations, (perfluoro)alkylations, acylations, and even cyanations. Most of these transformations involve the photochemical induced generation of a radical followed by its regioselective addition to arenes, heteroarenes, or alkenes, leading to the building of a new C(sp2)-C bond. The use of photoredox catalysis plays crucial roles in these reactions promoting electron transfer, enabling the generation of radical species and single electron either oxidation or reduction. Such reactions operating at room temperature allow the building of C-C bonds with high chemo-, regio-, or stereoselectivity. This review surveys the formation of C(sp2)-C bonds initiated by photoredox catalysis which involves a C(sp2)-H bond functionalization step, describes the advantages compared to traditional C(sp2)-H bond functionalizations, and presents mechanistic insights into the role played by the photoredox catalysts.Transition metal-catalyzed C-H bond functionalizations have been the focus of intensive research over the last decades for the formation of C-C bonds from unfunctionalized arenes, heteroarenes, alkenes. These direct transformations provide new approaches in synthesis with high atom- and step-economy compared to the traditional catalytic cross-coupling reactions. However, such methods still suffer from several limitations including functional group tolerance and the lack of regioselectivity. In addition, they often require harsh reaction conditions and some of them need the use of strong oxidant, in a stoichiometric amount, avoiding these processes to be truly eco-friendly. The use of photoredox catalysis has contributed to a significant expansion of the scope of C(sp2)-H bond functionalizations which include the direct arylations, (perfluoro)alkylations, acylations, and even cyanations. Most of these transformations involve the photochemical induced generation of a radical followed by its regioselective addition to arenes, heteroarenes, or alkenes, leading to the building of a new C(sp2)-C bond. The use of photoredox catalysis plays crucial roles in these reactions promoting electron transfer, enabling the generation of radical species and single electron either oxidation or reduction. Such reactions operating at room temperature allow the building of C-C bonds with high chemo-, regio-, or stereoselectivity. This review surveys the formation of C(sp2)-C bonds initiated by photoredox catalysis which involves a C(sp2)-H bond functionalization step, describes the advantages compared to traditional C(sp2)-H bond functionalizations, and presents mechanistic insights into the role played by the photoredox catalysts. Transition metal-catalyzed C–H bond functionalizations have been the focus of intensive research over the last decades for the formation of C–C bonds from unfunctionalized arenes, heteroarenes, alkenes. These direct transformations provide new approaches in synthesis with high atom- and step-economy compared to the traditional catalytic cross-coupling reactions. However, such methods still suffer from several limitations including functional group tolerance and the lack of regioselectivity. In addition, they often require harsh reaction conditions and some of them need the use of strong oxidant, in a stoichiometric amount, avoiding these processes to be truly eco-friendly. The use of photoredox catalysis has contributed to a significant expansion of the scope of C(sp²)–H bond functionalizations which include the direct arylations, (perfluoro)alkylations, acylations, and even cyanations. Most of these transformations involve the photochemical induced generation of a radical followed by its regioselective addition to arenes, heteroarenes, or alkenes, leading to the building of a new C(sp²)–C bond. The use of photoredox catalysis plays crucial roles in these reactions promoting electron transfer, enabling the generation of radical species and single electron either oxidation or reduction. Such reactions operating at room temperature allow the building of C–C bonds with high chemo-, regio-, or stereoselectivity. This review surveys the formation of C(sp²)–C bonds initiated by photoredox catalysis which involves a C(sp²)–H bond functionalization step, describes the advantages compared to traditional C(sp²)–H bond functionalizations, and presents mechanistic insights into the role played by the photoredox catalysts. Transition metal-catalyzed C–H bond functionalizations have been the focus of intensive research over the last decades for the formation of C–C bonds from unfunctionalized arenes, heteroarenes, alkenes. These direct transformations provide new approaches in synthesis with high atom- and step-economy compared to the traditional catalytic cross-coupling reactions. However, such methods still suffer from several limitations including functional group tolerance and the lack of regioselectivity. In addition, they often require harsh reaction conditions and some of them need the use of strong oxidant, in a stoichiometric amount, avoiding these processes to be truly eco-friendly. The use of photoredox catalysis has contributed to a significant expansion of the scope of C(sp2)–H bond functionalizations which include the direct arylations, (perfluoro)alkylations, acylations, and even cyanations. Most of these transformations involve the photochemical induced generation of a radical followed by its regioselective addition to arenes, heteroarenes, or alkenes, leading to the building of a new C(sp2)–C bond. The use of photoredox catalysis plays crucial roles in these reactions promoting electron transfer, enabling the generation of radical species and single electron either oxidation or reduction. Such reactions operating at room temperature allow the building of C–C bonds with high chemo-, regio-, or stereoselectivity. This review surveys the formation of C(sp2)–C bonds initiated by photoredox catalysis which involves a C(sp2)–H bond functionalization step, describes the advantages compared to traditional C(sp2)–H bond functionalizations, and presents mechanistic insights into the role played by the photoredox catalysts. |
| Author | Wang, Chang-Sheng Dixneuf, Pierre H Soulé, Jean-François |
| AuthorAffiliation | CNRS, ISCR UMR 6226 Univ Rennes |
| AuthorAffiliation_xml | – name: Univ Rennes – name: CNRS, ISCR UMR 6226 |
| Author_xml | – sequence: 1 givenname: Chang-Sheng surname: Wang fullname: Wang, Chang-Sheng – sequence: 2 givenname: Pierre H surname: Dixneuf fullname: Dixneuf, Pierre H – sequence: 3 givenname: Jean-François orcidid: 0000-0002-6593-1995 surname: Soulé fullname: Soulé, Jean-François email: jean-francois.soule@univ-rennes1.fr |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30011194$$D View this record in MEDLINE/PubMed https://univ-rennes.hal.science/hal-01862464$$DView record in HAL |
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| Snippet | Transition metal-catalyzed C–H bond functionalizations have been the focus of intensive research over the last decades for the formation of C–C bonds from... Transition metal-catalyzed C-H bond functionalizations have been the focus of intensive research over the last decades for the formation of C-C bonds from... |
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| SubjectTerms | Alkenes Alkylation ambient temperature Aromatic compounds aromatic hydrocarbons arylation Bonding Catalysis catalysts catalytic activity chemical bonding Chemical bonds Chemical reactions Chemical Sciences Chemical synthesis Cross coupling cross-coupling reactions Electron transfer Functional groups Hydrogen bonds Metals moieties oxidants Oxidation Oxidizing agents Photocatalysis Photochemicals photochemistry Photoredox catalysis Regioselectivity Stereoselectivity surveys Transformations Transition metals |
| Title | Photoredox Catalysis for Building C–C Bonds from C(sp2)–H Bonds |
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