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Stereoretentive H/D Exchange via an Electroactivated Heterogeneous Catalyst at sp 3 C–H Sites Bearing Amines or Alcohols
Author(s) -
Bhatia Souful,
Spahlinger Greg,
Boukhumseen Nehal,
Boll Quentin,
Li Zhenglong,
Jackson James E.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600719
Subject(s) - chemistry , ruthenium , catalysis , amine gas treating , deuterium , hydrogen–deuterium exchange , alcohol , aqueous solution , hydrogen , medicinal chemistry , organic chemistry , physics , quantum mechanics
This report describes a mild, aqueous‐phase strategy that enables stereoretentive C–H activation at sp 3 C–H sites bearing amine or alcohol groups. The transformation utilizes D 2 O to replace the hydrogen with deuterium while retaining stereochemistry. Electroactivated ruthenium particles, which are supported by an activated carbon cloth (Ru/ACC), catalyze this reaction on a timescale of minutes to hours. This yields optimal results at low current density and mild temperature.