A Redox‐Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions
We report a simple protocol for the photochemical Giese addition of C(sp3)‐centered radicals to a variety of electron‐poor olefins. The chemistry does not require external photoredox catalysts. Instead, it harnesses the excited‐state reactivity of 4‐alkyl‐1,4‐dihydropyridines (4‐alkyl‐DHPs) to gener...
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| Published in | Angewandte Chemie International Edition Vol. 58; no. 15; pp. 4953 - 4957 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
01.04.2019
Wiley Subscription Services, Inc John Wiley and Sons Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | We report a simple protocol for the photochemical Giese addition of C(sp3)‐centered radicals to a variety of electron‐poor olefins. The chemistry does not require external photoredox catalysts. Instead, it harnesses the excited‐state reactivity of 4‐alkyl‐1,4‐dihydropyridines (4‐alkyl‐DHPs) to generate alkyl radicals. Crucial for reactivity is the use of a catalytic amount of Ni(bpy)32+ (bpy=2,2′‐bipyridyl), which acts as an electron mediator to facilitate the redox processes involving fleeting and highly reactive intermediates.
A time to get, and a time to lose electrons: Electron mediators can alleviate limitations associated with the photochemistry of excited‐state intermediates, including short lifetimes and low electron transfer rates. The ability of a nickel complex to act as an electron shuttle assists the excited‐state reactivity of dihydropyridines 1 to enable a photochemical Giese addition of C(sp3)‐centered radicals to electron‐poor olefins. |
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| AbstractList | We report a simple protocol for the photochemical Giese addition of C(sp3)‐centered radicals to a variety of electron‐poor olefins. The chemistry does not require external photoredox catalysts. Instead, it harnesses the excited‐state reactivity of 4‐alkyl‐1,4‐dihydropyridines (4‐alkyl‐DHPs) to generate alkyl radicals. Crucial for reactivity is the use of a catalytic amount of Ni(bpy)32+ (bpy=2,2′‐bipyridyl), which acts as an electron mediator to facilitate the redox processes involving fleeting and highly reactive intermediates. We report a simple protocol for the photochemical Giese addition of C(sp3 )-centered radicals to a variety of electron-poor olefins. The chemistry does not require external photoredox catalysts. Instead, it harnesses the excited-state reactivity of 4-alkyl-1,4-dihydropyridines (4-alkyl-DHPs) to generate alkyl radicals. Crucial for reactivity is the use of a catalytic amount of Ni(bpy)3 2+ (bpy=2,2'-bipyridyl), which acts as an electron mediator to facilitate the redox processes involving fleeting and highly reactive intermediates.We report a simple protocol for the photochemical Giese addition of C(sp3 )-centered radicals to a variety of electron-poor olefins. The chemistry does not require external photoredox catalysts. Instead, it harnesses the excited-state reactivity of 4-alkyl-1,4-dihydropyridines (4-alkyl-DHPs) to generate alkyl radicals. Crucial for reactivity is the use of a catalytic amount of Ni(bpy)3 2+ (bpy=2,2'-bipyridyl), which acts as an electron mediator to facilitate the redox processes involving fleeting and highly reactive intermediates. We report a simple protocol for the photochemical Giese addition of C(sp(3))-centered radicals to a variety of electron-poor olefins. The chemistry does not require external photoredox catalysts. Instead, it harnesses the excited-state reactivity of 4-alkyl-1,4-dihydropyridines (4-alkyl-DHPs) to generate alkyl radicals. Crucial for reactivity is the use of a catalytic amount of Ni(bpy)(3)(2+) (bpy=2,2'-bipyridyl), which acts as an electron mediator to facilitate the redox processes involving fleeting and highly reactive intermediates. We report a simple protocol for the photochemical Giese addition of C(sp3)‐centered radicals to a variety of electron‐poor olefins. The chemistry does not require external photoredox catalysts. Instead, it harnesses the excited‐state reactivity of 4‐alkyl‐1,4‐dihydropyridines (4‐alkyl‐DHPs) to generate alkyl radicals. Crucial for reactivity is the use of a catalytic amount of Ni(bpy)32+ (bpy=2,2′‐bipyridyl), which acts as an electron mediator to facilitate the redox processes involving fleeting and highly reactive intermediates. A time to get, and a time to lose electrons: Electron mediators can alleviate limitations associated with the photochemistry of excited‐state intermediates, including short lifetimes and low electron transfer rates. The ability of a nickel complex to act as an electron shuttle assists the excited‐state reactivity of dihydropyridines 1 to enable a photochemical Giese addition of C(sp3)‐centered radicals to electron‐poor olefins. We report a simple protocol for the photochemical Giese addition of C(sp 3 )‐centered radicals to a variety of electron‐poor olefins. The chemistry does not require external photoredox catalysts. Instead, it harnesses the excited‐state reactivity of 4‐alkyl‐1,4‐dihydropyridines (4‐alkyl‐DHPs) to generate alkyl radicals. Crucial for reactivity is the use of a catalytic amount of Ni(bpy) 3 2+ (bpy=2,2′‐bipyridyl), which acts as an electron mediator to facilitate the redox processes involving fleeting and highly reactive intermediates. We report a simple protocol for the photochemical Giese addition of C(sp )-centered radicals to a variety of electron-poor olefins. The chemistry does not require external photoredox catalysts. Instead, it harnesses the excited-state reactivity of 4-alkyl-1,4-dihydropyridines (4-alkyl-DHPs) to generate alkyl radicals. Crucial for reactivity is the use of a catalytic amount of Ni(bpy) (bpy=2,2'-bipyridyl), which acts as an electron mediator to facilitate the redox processes involving fleeting and highly reactive intermediates. |
| Author | Perego, Luca Alessandro van Leeuwen, Thomas Buzzetti, Luca Melchiorre, Paolo |
| AuthorAffiliation | 1 ICREA —Catalan Institution for Research and Advanced Studies Passeig Lluís Companys 23 08010 Barcelona Spain 3 ICIQ —Institute of Chemical Research of Catalonia the Barcelona Institute of Science and Technology Avenida Països Catalans 16 43007 Tarragona Spain 2 IIT —Istituto Italiano di Tecnologia Laboratory of Asymmetric Catalysis and Photochemistry via Morego 30 16163 Genoa Italy |
| AuthorAffiliation_xml | – name: 1 ICREA —Catalan Institution for Research and Advanced Studies Passeig Lluís Companys 23 08010 Barcelona Spain – name: 3 ICIQ —Institute of Chemical Research of Catalonia the Barcelona Institute of Science and Technology Avenida Països Catalans 16 43007 Tarragona Spain – name: 2 IIT —Istituto Italiano di Tecnologia Laboratory of Asymmetric Catalysis and Photochemistry via Morego 30 16163 Genoa Italy |
| Author_xml | – sequence: 1 givenname: Thomas surname: van Leeuwen fullname: van Leeuwen, Thomas organization: ICIQ—Institute of Chemical Research of Catalonia the Barcelona Institute of Science and Technology – sequence: 2 givenname: Luca orcidid: 0000-0002-1096-8272 surname: Buzzetti fullname: Buzzetti, Luca organization: IIT—Istituto Italiano di Tecnologia – sequence: 3 givenname: Luca Alessandro surname: Perego fullname: Perego, Luca Alessandro organization: ICIQ—Institute of Chemical Research of Catalonia the Barcelona Institute of Science and Technology – sequence: 4 givenname: Paolo orcidid: 0000-0001-8722-4602 surname: Melchiorre fullname: Melchiorre, Paolo email: pmelchiorre@iciq.es organization: ICIQ—Institute of Chemical Research of Catalonia the Barcelona Institute of Science and Technology |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30747467$$D View this record in MEDLINE/PubMed |
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| Keywords | OXIDATION REAGENTS REDUCTION electron mediator photochemistry dihydropyridines ALKYLATION RADICALS HANTZSCH ESTERS synthetic methods nickel catalysis |
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| SSID | ssj0028806 |
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| Snippet | We report a simple protocol for the photochemical Giese addition of C(sp3)‐centered radicals to a variety of electron‐poor olefins. The chemistry does not... We report a simple protocol for the photochemical Giese addition of C(sp 3 )‐centered radicals to a variety of electron‐poor olefins. The chemistry does not... We report a simple protocol for the photochemical Giese addition of C(sp(3))-centered radicals to a variety of electron-poor olefins. The chemistry does not... We report a simple protocol for the photochemical Giese addition of C(sp )-centered radicals to a variety of electron-poor olefins. The chemistry does not... We report a simple protocol for the photochemical Giese addition of C(sp3 )-centered radicals to a variety of electron-poor olefins. The chemistry does not... |
| Source | Web of Science |
| SourceID | pubmedcentral proquest pubmed webofscience crossref wiley |
| SourceType | Open Access Repository Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 4953 |
| SubjectTerms | Alkenes Atmospheric chemistry Catalysis Catalysts Chemistry Chemistry, Multidisciplinary Communication Communications dihydropyridines electron mediator Electrons Harnesses Intermediates Nickel nickel catalysis Organic chemistry Photochemical reactions Photochemicals photochemistry Physical Sciences Radicals Science & Technology synthetic methods |
| Title | A Redox‐Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201814497 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000463739900026 https://www.ncbi.nlm.nih.gov/pubmed/30747467 https://www.proquest.com/docview/2196568133 https://www.proquest.com/docview/2188593817 https://pubmed.ncbi.nlm.nih.gov/PMC6519288 |
| Volume | 58 |
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