Stereoretentive H/D Exchange via an Electroactivated Heterogeneous Catalyst at sp3 C-H Sites Bearing Amines or Alcohols

• Published in: European journal of organic chemistry Vol. 2016; no. 24; pp. 4230 - 4235
• Main Authors: Bhatia, Souful, Spahlinger, Greg, Boukhumseen, Nehal, Boll, Quentin, Li, Zhenglong, Jackson, James E.
• Format: Journal Article
• Language: English
• Published: Weinheim Blackwell Publishing Ltd 01.08.2016; Wiley Subscription Services, Inc
• Subjects: C-H activation; Deuterium; Electrocatalysis; Heterogeneous catalysis; Stereoretentivity
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201600719

This report describes a mild, aqueous‐phase strategy that enables stereoretentive C–H activation at sp3 C–H sites bearing amine or alcohol groups. The transformation utilizes D2O 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. An electrocatalytic strategy is reported that allows stereoretentive and regioselective H/D exchange in amines, alcohols and amino acids. The conversions are performed at ambient pressure in D2O at 60–75 °C and 10 mA.