Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides
The use of alkylzinc bromides in the multicomponent Mannich reaction is described. Heteroleptic organozinc compounds were obtained in THF or 2-MeTHF by direct insertion of zinc dust into the C–Br bond of alkyl bromides. It was found that the presence of a stoichiometric amount of LiCl was essential...
Saved in:
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2024-11-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.20.239 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1849220826498334720 |
|---|---|
| author | Baptiste Leroux Alexis Beaufils Federico Banchini Olivier Jackowski Alejandro Perez-Luna Fabrice Chemla Marc Presset Erwan Le Gall |
| author_facet | Baptiste Leroux Alexis Beaufils Federico Banchini Olivier Jackowski Alejandro Perez-Luna Fabrice Chemla Marc Presset Erwan Le Gall |
| author_sort | Baptiste Leroux |
| collection | DOAJ |
| description | The use of alkylzinc bromides in the multicomponent Mannich reaction is described. Heteroleptic organozinc compounds were obtained in THF or 2-MeTHF by direct insertion of zinc dust into the C–Br bond of alkyl bromides. It was found that the presence of a stoichiometric amount of LiCl was essential for the efficiency of the subsequent three-component coupling with aldehydes and amines. A variety of primary, secondary, and tertiary organozinc reagents as well as secondary amines and aromatic aldehydes could be used for the straightforward preparation of α-branched amines. Interestingly, whereas previously reported work describing the preparation and reaction of organozinc iodides in acetonitrile showed higher reactivity of secondary organozinc reagents over primary ones, reactions in THF in the presence of LiCl led to opposite results, with higher reactivity of primary organozinc reagents. |
| format | Article |
| id | doaj-art-4b7b21f253ac485da4a8fbcb65eacfa9 |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-4b7b21f253ac485da4a8fbcb65eacfa92024-12-02T08:46:11ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972024-11-012012834283910.3762/bjoc.20.2391860-5397-20-239Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromidesBaptiste Leroux0Alexis Beaufils1Federico Banchini2Olivier Jackowski3Alejandro Perez-Luna4Fabrice Chemla5Marc Presset6Erwan Le Gall7Univ Paris-Est Créteil, CNRS, ICMPE, UMR 7182, 2 rue Henri Dunant, 94320 Thiais, France Univ Paris-Est Créteil, CNRS, ICMPE, UMR 7182, 2 rue Henri Dunant, 94320 Thiais, France Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, IPCM, 75005 Paris, France Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, IPCM, 75005 Paris, France Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, IPCM, 75005 Paris, France Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, IPCM, 75005 Paris, France Univ Paris-Est Créteil, CNRS, ICMPE, UMR 7182, 2 rue Henri Dunant, 94320 Thiais, France Univ Paris-Est Créteil, CNRS, ICMPE, UMR 7182, 2 rue Henri Dunant, 94320 Thiais, France The use of alkylzinc bromides in the multicomponent Mannich reaction is described. Heteroleptic organozinc compounds were obtained in THF or 2-MeTHF by direct insertion of zinc dust into the C–Br bond of alkyl bromides. It was found that the presence of a stoichiometric amount of LiCl was essential for the efficiency of the subsequent three-component coupling with aldehydes and amines. A variety of primary, secondary, and tertiary organozinc reagents as well as secondary amines and aromatic aldehydes could be used for the straightforward preparation of α-branched amines. Interestingly, whereas previously reported work describing the preparation and reaction of organozinc iodides in acetonitrile showed higher reactivity of secondary organozinc reagents over primary ones, reactions in THF in the presence of LiCl led to opposite results, with higher reactivity of primary organozinc reagents.https://doi.org/10.3762/bjoc.20.239alkyl bromidesbranched aminesmannich reactionmulticomponent reactionzinc |
| spellingShingle | Baptiste Leroux Alexis Beaufils Federico Banchini Olivier Jackowski Alejandro Perez-Luna Fabrice Chemla Marc Presset Erwan Le Gall Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides Beilstein Journal of Organic Chemistry alkyl bromides branched amines mannich reaction multicomponent reaction zinc |
| title | Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides |
| title_full | Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides |
| title_fullStr | Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides |
| title_full_unstemmed | Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides |
| title_short | Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides |
| title_sort | multicomponent synthesis of α branched amines using organozinc reagents generated from alkyl bromides |
| topic | alkyl bromides branched amines mannich reaction multicomponent reaction zinc |
| url | https://doi.org/10.3762/bjoc.20.239 |
| work_keys_str_mv | AT baptisteleroux multicomponentsynthesisofabranchedaminesusingorganozincreagentsgeneratedfromalkylbromides AT alexisbeaufils multicomponentsynthesisofabranchedaminesusingorganozincreagentsgeneratedfromalkylbromides AT federicobanchini multicomponentsynthesisofabranchedaminesusingorganozincreagentsgeneratedfromalkylbromides AT olivierjackowski multicomponentsynthesisofabranchedaminesusingorganozincreagentsgeneratedfromalkylbromides AT alejandroperezluna multicomponentsynthesisofabranchedaminesusingorganozincreagentsgeneratedfromalkylbromides AT fabricechemla multicomponentsynthesisofabranchedaminesusingorganozincreagentsgeneratedfromalkylbromides AT marcpresset multicomponentsynthesisofabranchedaminesusingorganozincreagentsgeneratedfromalkylbromides AT erwanlegall multicomponentsynthesisofabranchedaminesusingorganozincreagentsgeneratedfromalkylbromides |