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Aminopotassiation by Mixed Potassium/Lithium Amides: A Synthetic Path to Difficult to Access Phenethylamine Derivates
- Source :
- Angewandte Chemie (International Ed. in English)
- Publication Year :
- 2020
- Publisher :
- Wiley, 2020.
-
Abstract
- Insights gained from a comparison of aminometalation reactions with lithium amides, potassium amides and mixed lithium/potassium amides are presented. A combination of structural characterization, DFT calculations and electrophile reactions of aminometalated intermediates has shown the advantages of using a mixed metal strategy. While potassium amides fail to add, the lithium amides are uncontrollable and eliminated, yet the mixed K/Li amides deliver the best of both systems. Aminopotassiation proceeds to form the alkylpotassium species which has enhanced stability over its lithium counterpart allowing for its isolation and thereby its further characterization.<br />The use of a mixed‐metal system consisting of LiNR2/KOR increases the selectivity of the aminometalation of styrene derivatives in favour of a potassiated intermediate over a polymerization product. Crystal structures along with quantum chemical calculations and experimental investigations demonstrate the additional advantages of potassium over lithium or sodium for the stability of metalated phenylethylamines.
- Subjects :
- Phenethylamine
alkali metals
Mixed metal
010405 organic chemistry
Communication
potassium
Potassium
chemistry.chemical_element
General Chemistry
010402 general chemistry
Alkali metal
01 natural sciences
Combinatorial chemistry
Communications
Catalysis
0104 chemical sciences
Aminometalation
carbanions
chemistry.chemical_compound
chemistry
Electrophile
Lithium
synergistic effects
Carbanion
Subjects
Details
- ISSN :
- 15213773 and 14337851
- Volume :
- 59
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie International Edition
- Accession number :
- edsair.doi.dedup.....f95c66da8a036bd74105ca8f6aaaa0f3