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Ruthenium(II)biscarboxylate‐Catalyzed Hydrogen‐Isotope Exchange by Alkene C−H Activation
Author(s) -
Bechtoldt Alexander,
Ackermann Lutz
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201801601
Subject(s) - ruthenium , catalysis , chemistry , alkene , deuterium , selectivity , hydrogen , isotopic labeling , photochemistry , organic chemistry , physics , quantum mechanics
Ruthenium(II) biscarboxylate catalysis enabled efficient hydrogen isotope exchange of acrylic C−H bonds with user‐friendly D 2 O. The C−H labelling was characterized by excellent positional selectivity and a broad functional group tolerance. The deuteration was successfully conducted on 55 mmol scale with TONs of >1000, while mechanistic studies provided insights into ruthenium(II) oxidase catalysis. The obtained deuterated alkenes enabled the synthesis of labeled standards for mass spectrometry of irradiated foodstuffs.