Direct Synthesis of Allyl Amines with 2‐Nitrosulfonamide Derivatives via the Tsuji‐Trost Reaction
Abstract The Tsuji‐Trost Reaction is a palladium‐catalysed allylation of nucleophiles that consists in the reaction of a nitrogen, carbon or oxygen‐based nucleophiles with an allylic substrate bearing a leaving group. Here we present the use of 2‐nitrosulfonamide derivatives as nucleophile, which ar...
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2021-12-01
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| Series: | ChemistryOpen |
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| Online Access: | https://doi.org/10.1002/open.202100147 |
| _version_ | 1818362982247170048 |
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| author | Corentin Bon Dr. Paola B. Arimondo Dr. Ludovic Halby |
| author_facet | Corentin Bon Dr. Paola B. Arimondo Dr. Ludovic Halby |
| author_sort | Corentin Bon |
| collection | DOAJ |
| description | Abstract The Tsuji‐Trost Reaction is a palladium‐catalysed allylation of nucleophiles that consists in the reaction of a nitrogen, carbon or oxygen‐based nucleophiles with an allylic substrate bearing a leaving group. Here we present the use of 2‐nitrosulfonamide derivatives as nucleophile, which are reactive under mild conditions. 2‐nitrosulfonyl groups are well‐known dual protective activator groups easy to introduce in any type of amine substrates. The resulting 2‐nitrosulfonamide derivatives are ideal substrates for the Tsuji‐Trost reaction to afford a convenient and flexible access to primary and dissymmetric secondary allyl amines. The optimised procedure is flexible (for solvent, temperature, functional groups) and has been applied with good to excellent yield to access to a wide range of allyl amine derivatives. |
| first_indexed | 2024-12-13T21:41:14Z |
| format | Article |
| id | doaj.art-c63cbf98c21c4f2b8a15a24ec63a8712 |
| institution | Directory Open Access Journal |
| issn | 2191-1363 |
| language | English |
| last_indexed | 2024-12-13T21:41:14Z |
| publishDate | 2021-12-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj.art-c63cbf98c21c4f2b8a15a24ec63a87122022-12-21T23:30:32ZengWiley-VCHChemistryOpen2191-13632021-12-0110121166116910.1002/open.202100147Direct Synthesis of Allyl Amines with 2‐Nitrosulfonamide Derivatives via the Tsuji‐Trost ReactionCorentin Bon0Dr. Paola B. Arimondo1Dr. Ludovic Halby2Epigenetic Chemical Biology Department of Structural Biology and Chemistry Institut Pasteur UMR3523 CNRS 75015 Paris FranceEpigenetic Chemical Biology Department of Structural Biology and Chemistry Institut Pasteur UMR3523 CNRS 75015 Paris FranceEpigenetic Chemical Biology Department of Structural Biology and Chemistry Institut Pasteur UMR3523 CNRS 75015 Paris FranceAbstract The Tsuji‐Trost Reaction is a palladium‐catalysed allylation of nucleophiles that consists in the reaction of a nitrogen, carbon or oxygen‐based nucleophiles with an allylic substrate bearing a leaving group. Here we present the use of 2‐nitrosulfonamide derivatives as nucleophile, which are reactive under mild conditions. 2‐nitrosulfonyl groups are well‐known dual protective activator groups easy to introduce in any type of amine substrates. The resulting 2‐nitrosulfonamide derivatives are ideal substrates for the Tsuji‐Trost reaction to afford a convenient and flexible access to primary and dissymmetric secondary allyl amines. The optimised procedure is flexible (for solvent, temperature, functional groups) and has been applied with good to excellent yield to access to a wide range of allyl amine derivatives.https://doi.org/10.1002/open.202100147allylation reactionsconjugated allyl aminesnosyl groupspalladiumTsuji-Trost reactions |
| spellingShingle | Corentin Bon Dr. Paola B. Arimondo Dr. Ludovic Halby Direct Synthesis of Allyl Amines with 2‐Nitrosulfonamide Derivatives via the Tsuji‐Trost Reaction ChemistryOpen allylation reactions conjugated allyl amines nosyl groups palladium Tsuji-Trost reactions |
| title | Direct Synthesis of Allyl Amines with 2‐Nitrosulfonamide Derivatives via the Tsuji‐Trost Reaction |
| title_full | Direct Synthesis of Allyl Amines with 2‐Nitrosulfonamide Derivatives via the Tsuji‐Trost Reaction |
| title_fullStr | Direct Synthesis of Allyl Amines with 2‐Nitrosulfonamide Derivatives via the Tsuji‐Trost Reaction |
| title_full_unstemmed | Direct Synthesis of Allyl Amines with 2‐Nitrosulfonamide Derivatives via the Tsuji‐Trost Reaction |
| title_short | Direct Synthesis of Allyl Amines with 2‐Nitrosulfonamide Derivatives via the Tsuji‐Trost Reaction |
| title_sort | direct synthesis of allyl amines with 2 nitrosulfonamide derivatives via the tsuji trost reaction |
| topic | allylation reactions conjugated allyl amines nosyl groups palladium Tsuji-Trost reactions |
| url | https://doi.org/10.1002/open.202100147 |
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