Directed ortho metalation of N, N-diethylbenzamides. Silicon protection of ortho sites and the o-methyl group

RJ Mills, NJ Taylor, V Snieckus

Index: Mills, Robert J.; Taylor, Nicholas J.; Snieckus, Victor Journal of Organic Chemistry, 1989 ,  vol. 54,  # 18  p. 4372 - 4385

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Citation Number: 130

Abstract

New general methodology of value in aromatic chemistry based on silicon protection of preferred ortho metalation sites in benzamides and o-methyl groups in o-toluamides (1, 2, Scheme I) is described. According to these methodologies, routes (Schemes I1 and V) to 1, 2, 5-, 1, 2, 4, 5-, and 1, 2, 3-substituted aromatics with a variety of functionalities and oxidation states have been developed (Tables I and 11). These tactics are used for the ...