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

Pei Liu; Jinghua Tang; Xiaoming Zeng

doi:10.1021/acs.orglett.6b02784

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

Org Lett. 2016 Nov 4;18(21):5536-5539. doi: 10.1021/acs.orglett.6b02784. Epub 2016 Oct 24.

Authors

Pei Liu¹, Jinghua Tang¹, Xiaoming Zeng^{1

2

3}

Affiliations

¹ Center for Organic Chemistry, Frontier Institute of Science and Technology, Xi'an Jiaotong University , Xi'an 710054, China.
² Department of Chemistry, Northeast Normal University , Changchun 130024, China.
³ State Key Laboratory of Elemento-organic Chemistry, Nankai University , Tianjin 300071, China.

PMID: 27774791
DOI: 10.1021/acs.orglett.6b02784

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't