Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst
This report describes a highly enantioselective oxidative sp3 C–H arylation of N-aryltetrahydroisoquinolines (THIQs) through a dual catalysis platform. The combination of the photoredox catalyst, [Ir(ppy)2(dtbbpy)]PF6, and chiral copper catalysts provide a mild and highly effective sp3 C–H asymmetri...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2016-12-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.12.260 |
| _version_ | 1819062866195513344 |
|---|---|
| author | Pierre Querard Inna Perepichka Eli Zysman-Colman Chao-Jun Li |
| author_facet | Pierre Querard Inna Perepichka Eli Zysman-Colman Chao-Jun Li |
| author_sort | Pierre Querard |
| collection | DOAJ |
| description | This report describes a highly enantioselective oxidative sp3 C–H arylation of N-aryltetrahydroisoquinolines (THIQs) through a dual catalysis platform. The combination of the photoredox catalyst, [Ir(ppy)2(dtbbpy)]PF6, and chiral copper catalysts provide a mild and highly effective sp3 C–H asymmetric arylation of THIQs. |
| first_indexed | 2024-12-21T15:05:35Z |
| format | Article |
| id | doaj.art-52917e448a3c471ba24512b8d4a70acd |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-21T15:05:35Z |
| publishDate | 2016-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-52917e448a3c471ba24512b8d4a70acd2022-12-21T18:59:27ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-12-011212636264310.3762/bjoc.12.2601860-5397-12-260Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalystPierre Querard0Inna Perepichka1Eli Zysman-Colman2Chao-Jun Li3Department of Chemistry, FQRNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, CanadaDepartment of Chemistry, FQRNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, CanadaOrganic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife, KY16 9ST, UKDepartment of Chemistry, FQRNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, CanadaThis report describes a highly enantioselective oxidative sp3 C–H arylation of N-aryltetrahydroisoquinolines (THIQs) through a dual catalysis platform. The combination of the photoredox catalyst, [Ir(ppy)2(dtbbpy)]PF6, and chiral copper catalysts provide a mild and highly effective sp3 C–H asymmetric arylation of THIQs.https://doi.org/10.3762/bjoc.12.260C–H arylationcopper catalystenantioselectivityvisible light |
| spellingShingle | Pierre Querard Inna Perepichka Eli Zysman-Colman Chao-Jun Li Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst Beilstein Journal of Organic Chemistry C–H arylation copper catalyst enantioselectivity visible light |
| title | Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst |
| title_full | Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst |
| title_fullStr | Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst |
| title_full_unstemmed | Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst |
| title_short | Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst |
| title_sort | copper catalyzed asymmetric sp3 c h arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst |
| topic | C–H arylation copper catalyst enantioselectivity visible light |
| url | https://doi.org/10.3762/bjoc.12.260 |
| work_keys_str_mv | AT pierrequerard coppercatalyzedasymmetricsp3charylationoftetrahydroisoquinolinemediatedbyavisiblelightphotoredoxcatalyst AT innaperepichka coppercatalyzedasymmetricsp3charylationoftetrahydroisoquinolinemediatedbyavisiblelightphotoredoxcatalyst AT elizysmancolman coppercatalyzedasymmetricsp3charylationoftetrahydroisoquinolinemediatedbyavisiblelightphotoredoxcatalyst AT chaojunli coppercatalyzedasymmetricsp3charylationoftetrahydroisoquinolinemediatedbyavisiblelightphotoredoxcatalyst |