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Pd-catalysed ortho-alkoxylation of benzamides N-protected with an iminophosphorane functionality

AutorVilluendas, Pedro ; Serrano, Elena ; Urriolabeitia, Esteban P.
Fecha de publicación2015
EditorRoyal Society of Chemistry (Great Britain)
CitaciónNew Journal of Chemistry 39(4): 3077-3083 (2015)
ResumenThe oxidative coupling of keto-stabilised iminophosphoranes (IPs) Ph3P=NC(O)C6HxRy with alcohols R′OH affords the alkoxylated species Ph3P=NC(O)C6Hx-1Ry-2-OR′. The process is catalysed by 10% PdCl2(NCMe)2, uses oxone® as an oxidant and alcohol R′OH as a source of OR′ groups and reaction solvent. The reaction takes place at room temperature regioselectively at the ortho-position of the benzamide ring, gives only the mono-alkoxylated derivatives, and shows tolerance to a variety of functional groups and different primary and secondary alcohols. Better yields were obtained when the aryl ring contains electron-releasing substituents (OMe, Me). The iminophosphorane moiety plays a dual role as the protecting/directing group, and can be hydrolysed to give the corresponding free benzamide.
Identificadoresdoi: 10.1039/C5NJ00189G
e-issn: 1369-9261
issn: 1144-0546
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