American Chemical Society
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Site-Selective Silylation of Aliphatic C–H Bonds Mediated by [1,5]-Hydrogen Transfer: Synthesis of α‑Sila Benzamides

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posted on 2016-10-24, 11:35 authored by Pei Liu, Jinghua Tang, Xiaoming Zeng
The first example of site-selective silylation of C­(sp3)–H bonds mediated by a [1,5]-hydrogen transfer is reported. This reaction occurs selectively at the α-position of benzamides with a combination of tert-butylmagnesium chloride and a catalytic amount of 4,4′-di-tert-butylbipyridine (dtbpy) ligand and provides a facile route for the creation of biologically interesting α-sila benzamides. Late-stage functionalization of the incorporated silyl moieties facilitates the synthesis of N-formyl, cis-enamine, β-hydroxyl, amino, and pyrrole-containing derivatives.