Catalytic Generation and Chemoselective Transfer of Nucleophilic Hydrides from Dihydrogen.
- Resource Type
- Article
- Authors
- Pape, Felix; Brechmann, Lea T.; Teichert, Johannes F.
- Source
- Chemistry - A European Journal. 1/18/2019, Vol. 25 Issue 4, p985-988. 4p.
- Subject
- *COPPER catalysts
*HYDROGENATION
*CARBENES
*CHLORIDES
*CHEMOSELECTIVITY
*NUCLEOPHILIC catalysis
- Language
- ISSN
- 0947-6539
Copper(I)–N‐heterocyclic‐carbene (NHC) complexes enabled the catalytic generation of nucleophilic hydrides from dihydrogen (H2) and their subsequent transfer to allylic chlorides. The highly chemoselective catalyst displayed no concomitant hydrogenation reactivity; in fact, the terminal double bond formed in the hydride transfer remained intact. Switching to deuterium gas (D2) allowed for regioselective monodeuteration with excellent isotope incorporation. Copper hydride replacement. Dihydrogen (H2) can be used as source for hydride nucleophiles in a chemo‐ and regioselective allylic substitution. Switching to D2 allows for selective monodeuteration. [ABSTRACT FROM AUTHOR]