Water Compatible Hypophosphites- d2 Reagents: Deuteration Reaction via Deutero-deiodination in Aqueous Solution

Org Lett. 2020 Mar 6;22(5):1736-1741. doi: 10.1021/acs.orglett.0c00001. Epub 2020 Feb 21.

Abstract

Contrary to conventional deuteration approaches which typically entail deuterated solvents and/or moisture exclusion, an unprecedented deutero-deiodination reaction attainable in aqueous (H2O) solution is presented herein. By utilizing the stability of inorganic deuterated calcium/sodium hypophosphites against wayward H/D isotopic exchange within pH 2.5-11.7, these shelf-stable, nontoxic, cost-effective, and environmentally benign deuteration reagents mediate deuteration of a broad range alkyl and aryl iodides with ample isotopic incorporation in aqueous (H2O) solution.

Publication types

  • Research Support, Non-U.S. Gov't