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Angewandte Chemie (International ed.), 2019-02, Vol.58 (9), p.2875-2878
International ed. in English, 2019

Details

Autor(en) / Beteiligte
Titel
Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis
Ist Teil von
  • Angewandte Chemie (International ed.), 2019-02, Vol.58 (9), p.2875-2878
Auflage
International ed. in English
Ort / Verlag
Germany: Wiley Subscription Services, Inc
Erscheinungsjahr
2019
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
  • Primary aminoboranes (RNHBR2), which are readily available by spontaneous dehydrocoupling of amines and boranes cleanly react at room temperature with aldehydes to give aldimines. The overall transformation from amines to aldimines can be conveniently performed by a sequential one‐pot reaction. This synthetic strategy is especially useful for electron poor and bulky amines which are reluctant to react with aldehydes under dehydration conditions. Using a Glorius robustness screen, we show that this methodology is chemoselective, and functional group tolerant. Computational and experimental data support the irreversible formation of the aldimine product in marked contrast with traditional methods. Simple and powerful: Primary aminoboranes (RNHBR2) are powerful tools for the chemoselective, functional‐group tolerant, and widely applicable synthesis of aldimines. According to DFT calculations and experimental methods, this reaction proceeds in a non‐reversible way that is orthogonal to, and outperforms, conventional dehydration methods.

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