Mannich Reaction of Secondary Benzylzinc Reagents: Synthesis of α,β‐Disubstituted β‐Arylethylamines
Abstract The organometallic multicomponent Manich reaction of secondary benzylzinc compounds is described. These organometallic reagents were efficiently prepared by direct metalation of (1‐bromoethyl)benzenes in tetrahydrofuran with zinc dust. Their subsequent multicomponent Mannich coupling with amines and aldehydes allowed the straightforward preparation of a large variety of α,β‐disubstituted β‐arylethylamines in yields ranging from 13% to 79%. This reaction was found to require the use of a heated mixture of tetrahydrofuran and acetonitrile, tetrahydrofuran being essential to reach good yields and acetonitrile ensuring reproducibility.
Authors
- Olivier Jackowski (ORCID: https://orcid.org/0000-0001-9162-3294)
- Federico Banchini (ORCID: https://orcid.org/0000-0002-8240-5911)
- Baptiste Leroux
- Alejandro Pérez‐Luna
- Erwan Le Gall (ORCID: https://orcid.org/0000-0002-8972-3971)
- Fabrice Chemla (ORCID: https://orcid.org/0000-0001-6172-1504)
- Marc Presset (ORCID: https://orcid.org/0000-0003-0994-5572)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Université Paris-Est Créteil (FR)
- Sorbonne Université (FR)
- Institut de Chimie et des Matériaux Paris-Est (FR)
- Institut Parisien de Chimie Moléculaire (FR)
Publication Details
- Journal
- Asian Journal of Organic Chemistry
- Published
- 2025-04-08
- DOI
- https://doi.org/10.1002/ajoc.202500091
- Citations
- 2
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Agence Nationale de la Recherche