Formal meta-specific intramolecular Friedel–Crafts allylic alkylation of phenols through a spirocyclization–dienone–phenol rearrangement cascade

Autor:	Mariko Yoshida, Tetsuhiro Nemoto, Yasumasa Hamada, Tomoyuki Nozaki
Rok vydání:	2013
Předmět:	inorganic chemicals organic chemicals Organic Chemistry chemistry.chemical_element Biochemistry Medicinal chemistry Catalysis Tsuji–Trost reaction chemistry.chemical_compound chemistry Yield (chemistry) Intramolecular force Drug Discovery Phenol Phenols Friedel–Crafts reaction Palladium
Zdroj:	Tetrahedron. 69:9609-9615
ISSN:	0040-4020
DOI:	10.1016/j.tet.2013.09.042
Popis:	Formal meta-specific intramolecular Friedel–Crafts allylic alkylation of phenols was achieved based on spirocyclization–dienone–phenol rearrangement cascades. Systematic screening of acid catalysts revealed that Sc(OTf)3 was a highly effective catalyst for dienone–phenol rearrangement of spiro[4.5]cyclohexadienones. Using 5 mol % of Sc(OTf)3 as the promoter, various spirocyclic substrates were transformed into the corresponding phenol derivatives in good to excellent yield. Furthermore, the one-pot sequential spirocyclization–dienone–phenol rearrangement proceeded using a palladium and scandium multi-catalytic system or a triphenylmethyl cation single-catalyst system, providing the corresponding meta-allylated phenol derivatives in excellent yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::387927456c0582e30c20e67a288d133a https://doi.org/10.1016/j.tet.2013.09.042 Zobrazit plný text záznamu Full Text from ScienceDirect