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Catalytic Generation and Chemoselective Transfer of Nucleophilic Hydrides from Dihydrogen
Author(s) -
Pape Felix,
Brechmann Lea T.,
Teichert Johannes F.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201805530
Subject(s) - nucleophile , catalysis , regioselectivity , chemistry , carbene , allylic rearrangement , reactivity (psychology) , hydride , kinetic isotope effect , deuterium , medicinal chemistry , organic chemistry , combinatorial chemistry , photochemistry , hydrogen , medicine , physics , alternative medicine , pathology , quantum mechanics
Copper(I)–N‐heterocyclic‐carbene (NHC) complexes enabled the catalytic generation of nucleophilic hydrides from dihydrogen (H 2 ) 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 (D 2 ) allowed for regioselective monodeuteration with excellent isotope incorporation.