16463-22-2Relevant academic research and scientific papers
Visible light driven hydro-/deuterodefunctionalization of anilines
Majek, Michal,Filace, Fabiana,Von Wangelin, Axel Jacobi
supporting information, p. 4518 - 4522 (2015/03/18)
The defunctionalization of anilines is an important strategy in aromatic-substitution chemistry. Herein, we report on visible light mediated hydro- and deuterodediazonations in solutions of DMF. The mild reaction conditions (DMF, RT, no additives) tolerate various functional groups and allow the site-specific introduction of D atoms to the arene. Mechanistic investigations indicate the participation of photoredox and radical chain pathways and competing abstraction of methyl and formyl hydrogen atoms from DMF.
Selective copper- or silver-catalyzed decarboxylative deuteration of aromatic carboxylic acids
Rudzki, Martin,Alcalde-Aragones, Ana,Dzik, Wojciech I.,Rodriguez, Nuria,Goossen, Lukas J.
experimental part, p. 184 - 193 (2012/03/26)
The practical utility of decarboxylative transformations in organic synthesis is discussed, and the decarboxylative deuteration of (hetero)aromatic carboxylic acids is disclosed as a further example. Various monodeuterated arenes were synthesized under mild conditions, in a single step from easily accessible aromatic carboxylic acids and deuterium oxide. Copper catalysts were found to have the widest scope, but silver catalysts are superior for some ortho-substituted benzoates. A few substrates, e.g. quinoline-2-carboxylic acid, decarboxylate even in the absence of a metal catalyst. Georg Thieme Verlag Stuttgart · New York.
