Nucleus-and side-chain fluorinated 3-substituted indoles by a suitable combination of organometallic and radical chemistry

…, A Cipiciani, R Ruzziconi, S Spizzichino

Index: Bellezza, Francesca; Cipiciani, Antonio; Ruzziconi, Renzo; Spizzichino, Sara Journal of Fluorine Chemistry, 2008 , vol. 129, # 2 p. 97 - 107

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Citation Number: 7

Abstract

Regioselectively fluoro-, trifluoromethyl-and trifluoromethoxy-substituted 3- methyleneindolines have been prepared using a four-step procedure involving metalation/ bromination of fluorinated Boc-protected anilines, N-propargylation of the resulting o- bromoarylcarbamate and reductive radical cyclization of the product with tributyltin hydride/AIBN. 3-Methyleneindolines, as valuable, versatile intermediates, can be ...