Pd-catalysed ortho-alkoxylation of benzamides N-protected with an iminophosphorane functionality
作者： Pedro Villuendas , Elena Serrano , Esteban P Urriolabeitia , None
DOI: 10.1039/C5NJ00189G
关键词: Aryl 、 Ring (chemistry) 、 Medicinal chemistry 、 Chemistry 、 Oxidative coupling of methane 、 Hydrolysis 、 Alcohol 、 Organic chemistry 、 Moiety 、 Solvent 、 Benzamide
摘要: The oxidative coupling of keto-stabilised iminophosphoranes (IPs) Ph3PNC(O)C6HxRy with alcohols R′OH affords the alkoxylated species Ph3PNC(O)C6Hx−1Ry-2-OR′. process is catalysed by 10% PdCl2(NCMe)2, uses oxone® as an oxidant and alcohol a source OR′ groups reaction solvent. takes place at room temperature regioselectively ortho-position benzamide ring, gives only mono-alkoxylated derivatives, shows tolerance to variety functional different primary secondary alcohols. Better yields were obtained when aryl ring contains electron-releasing substituents (OMe, Me). iminophosphorane moiety plays dual role protecting/directing group, can be hydrolysed give corresponding free benzamide.
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