Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in RhII-catalyzed X–H insertion reactions
N-Alkyl α-diazo-γ-butyrolactams, previously found to be unstable and to undergo unproductive dimerization to bishydrazones, were successfully converted immediately to various X–H insertion products with alcohols, aromatic amines and thiols via an in situ RhII-catalyzed reaction. With aliphatic amine...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2020-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.16.55 |
| _version_ | 1818606713193889792 |
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| author | Maria Eremeyeva Daniil Zhukovsky Dmitry Dar’in Mikhail Krasavin |
| author_facet | Maria Eremeyeva Daniil Zhukovsky Dmitry Dar’in Mikhail Krasavin |
| author_sort | Maria Eremeyeva |
| collection | DOAJ |
| description | N-Alkyl α-diazo-γ-butyrolactams, previously found to be unstable and to undergo unproductive dimerization to bishydrazones, were successfully converted immediately to various X–H insertion products with alcohols, aromatic amines and thiols via an in situ RhII-catalyzed reaction. With aliphatic amines or unreactive, sterically hindered anilines, the reactions tended to yield enamine adducts. |
| first_indexed | 2024-12-16T14:15:13Z |
| format | Article |
| id | doaj.art-d04187155ed746caafef048f2bf6ba2c |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T14:15:13Z |
| publishDate | 2020-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-d04187155ed746caafef048f2bf6ba2c2022-12-21T22:28:38ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-04-0116160761010.3762/bjoc.16.551860-5397-16-55Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in RhII-catalyzed X–H insertion reactionsMaria Eremeyeva0Daniil Zhukovsky1Dmitry Dar’in2Mikhail Krasavin3Laboratory of Chemical Pharmacology, Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii prospect, Peterhof 198504, Russian FederationLaboratory of Chemical Pharmacology, Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii prospect, Peterhof 198504, Russian FederationLaboratory of Chemical Pharmacology, Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii prospect, Peterhof 198504, Russian FederationLaboratory of Chemical Pharmacology, Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii prospect, Peterhof 198504, Russian FederationN-Alkyl α-diazo-γ-butyrolactams, previously found to be unstable and to undergo unproductive dimerization to bishydrazones, were successfully converted immediately to various X–H insertion products with alcohols, aromatic amines and thiols via an in situ RhII-catalyzed reaction. With aliphatic amines or unreactive, sterically hindered anilines, the reactions tended to yield enamine adducts.https://doi.org/10.3762/bjoc.16.55in situ reactionsn-alkyl 2-pyrrolidonesrhii-catalyzed insertion reactionsstability of diazo compounds |
| spellingShingle | Maria Eremeyeva Daniil Zhukovsky Dmitry Dar’in Mikhail Krasavin Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in RhII-catalyzed X–H insertion reactions Beilstein Journal of Organic Chemistry in situ reactions n-alkyl 2-pyrrolidones rhii-catalyzed insertion reactions stability of diazo compounds |
| title | Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in RhII-catalyzed X–H insertion reactions |
| title_full | Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in RhII-catalyzed X–H insertion reactions |
| title_fullStr | Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in RhII-catalyzed X–H insertion reactions |
| title_full_unstemmed | Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in RhII-catalyzed X–H insertion reactions |
| title_short | Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in RhII-catalyzed X–H insertion reactions |
| title_sort | preparation and in situ use of unstable n alkyl α diazo γ butyrolactams in rhii catalyzed x h insertion reactions |
| topic | in situ reactions n-alkyl 2-pyrrolidones rhii-catalyzed insertion reactions stability of diazo compounds |
| url | https://doi.org/10.3762/bjoc.16.55 |
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