One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates
Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodol...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.316 |
| _version_ | 1818413945230196736 |
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| author | Joshua P. Barham Matthew P. John John A. Murphy |
| author_facet | Joshua P. Barham Matthew P. John John A. Murphy |
| author_sort | Joshua P. Barham |
| collection | DOAJ |
| description | Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible light-assisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields. |
| first_indexed | 2024-12-14T11:11:16Z |
| format | Article |
| id | doaj.art-a96bd4468021480aa3ae423e95b2a664 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T11:11:16Z |
| publishDate | 2014-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-a96bd4468021480aa3ae423e95b2a6642022-12-21T23:04:16ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-12-011012981298810.3762/bjoc.10.3161860-5397-10-316One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediatesJoshua P. Barham0Matthew P. John1John A. Murphy2WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United KingdomGlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United KingdomWestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United KingdomNucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible light-assisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.https://doi.org/10.3762/bjoc.10.316iminium saltorganometallicoxidative functionalisationphotoredox catalysistetrahydroisoquinoline |
| spellingShingle | Joshua P. Barham Matthew P. John John A. Murphy One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates Beilstein Journal of Organic Chemistry iminium salt organometallic oxidative functionalisation photoredox catalysis tetrahydroisoquinoline |
| title | One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates |
| title_full | One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates |
| title_fullStr | One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates |
| title_full_unstemmed | One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates |
| title_short | One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates |
| title_sort | one pot functionalisation of n substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates |
| topic | iminium salt organometallic oxidative functionalisation photoredox catalysis tetrahydroisoquinoline |
| url | https://doi.org/10.3762/bjoc.10.316 |
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