Angewandte Chemie International Edition · 2018 · 256 citations · 57 references
Natural SciencesChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistryReaction EngineeringCarboxylic AcidsCarboxylic DerivativesOrganic SynthesisAliphatic Carboxylic AcidsAromatic Carboxylic AcidsCarboxylic Acid Derivative SynthesisCarboxylic Acid SynthesisDeuteration ChemistryDeuterium ChemistryNatural Product Derivatives
Abstract We report a general, practical, and scalable means of preparing deuterated aldehydes from aromatic and aliphatic carboxylic acids with D 2 O as an inexpensive deuterium source. The use of Ph 3 P as an O‐atom transfer reagent can facilitate the deoxygenation of aromatic acids, while Ph 2 POEt is a better O‐atom transfer reagent for aliphatic acids. The highly precise deoxygenation of complex carboxylic acids makes this protocol promising for late‐stage deoxygenative deuteration of natural product derivatives and pharmaceutical compounds.
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Photoredox-catalyzed deuteration and tritiation of pharmaceutical compounds
Yong Yao Loh, Kazunori Nagao, Andrew J. Hoover et al. · Science · 2017 · 571 citations