Sodium Butylated Hydroxytoluene: A Functional Group Tolerant, Eco‐Friendly Base for Solvent‐Free, Pd‐Catalysed Amination

Autor:	Volodymyr Semeniuchenko, Wilfried M. Braje, Michael G. Organ
Rok vydání:	2021
Předmět:	010405 organic chemistry ved/biology Sodium Organic Chemistry ved/biology.organism_classification_rank.species General Chemistry Butylated Hydroxytoluene 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences PEPPSI chemistry.chemical_compound Nucleophile chemistry Functional group Solvents Butylated hydroxytoluene Organic chemistry Carbene Amination Conjugate acid
Zdroj:	Chemistry – A European Journal. 27:12535-12539
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.202101617
Popis:	NaBHT (sodium 2,6-di-tert-butyl-4-methylphenolate), a strong, but hindered and lipophilic base, has been effectively paired with similarly lipophilic, high-reactivity Pd-NHC (N-heterocyclic carbene) catalysts to produce an ideal combination for performing solvent-free (melt) cross-coupling amination. The mild nucleophilicity of NaBHT, coupled with the anti-oxidant properties of its conjugate acid byproduct, BHT means the process seems to have no functional group incompatibilities. Highly effective coupling of base-sensitive and redox-active functional groups was observed in all cases with only 0.1-0.2 mol percent catalyst. Comparisons using the standard base for this reaction, KOtBu, led to poor couplings or complete degradation in most applications - only NaBHT works.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0765f41d20b5ccc26073eaecb021c6be https://doi.org/10.1002/chem.202101617 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
Nepřihlášeným uživatelům se plný text nezobrazuje	K zobrazení výsledku je třeba se přihlásit.