Shifted Selectivity in Protonation Enables the Mild Deuteration of Arenes Through Catalytic Amounts of Bronsted Acids in Deuterated Methanol

Autor:	Anja Hubert, Oliver Fischer, Markus R. Heinrich
Rok vydání:	2020
Předmět:	chemistry.chemical_compound Acid catalysis chemistry Organic Chemistry Functional group Deuterated methanol Protonation Methanol Selectivity Brønsted–Lowry acid–base theory Combinatorial chemistry Catalysis
Zdroj:	The Journal of Organic Chemistry. 85:11856-11866
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.0c01604
Popis:	Taking advantage of the "differentiating effect" of the solvent methanol, deuterations of electron-rich aromatic systems can be carried out under mild acid catalysis and thus under far milder conditions than known so far. The exceptional functional group tolerance observed under the optimized conditions, which even includes highly acid-labile groups, results from a hitherto unexploited shifted selectivity in protonation, and enabled simple and straightforward access to complex deuterium-labeled compounds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::bce43bcf4f8c199d813678304fcbd2fe https://doi.org/10.1021/acs.joc.0c01604 Zobrazit plný text záznamu