Synthesis of silyl iron hydride via Si–H activation and its dual catalytic application in the hydrosilylation of carbonyl compounds and dehydration of benzamides

Shishuai Ren; Shangqing Xie; Tingting Zheng; Yangyang Wang; Shilu Xu; Benjing Xue; Xiaoyan Li; Hongjian Sun; Olaf Fuhr; Dieter Fenske

doi:10.1039/C8DT00289D

Synthesis of silyl iron hydride via Si–H activation and its dual catalytic application in the hydrosilylation of carbonyl compounds and dehydration of benzamides†

Shishuai Ren,‡^a Shangqing Xie,‡^a Tingting Zheng,‡^ab Yangyang Wang,‡^ac Shilu Xu,^a Benjing Xue,^a Xiaoyan Li,

^a Hongjian Sun,

*^a Olaf Fuhr^d and Dieter Fenske^d

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* Corresponding authors

^a School of Chemistry and Chemical Engineering, Key Laboratory of Special Functional Aggregated Materials, Ministry of Education, Shandong University, Shanda Nanlu 27, 250199 Jinan, People's Republic of China
E-mail: hjsun@sdu.edu.cn

^b Department of Chemistry, Capital Normal University, 100037 Beijing, People's Republic of China

^c College of Chemistry and Chemical Engineering, Northwest Normal University, 730070 Lanzhou, PR China

^d Institut für Nanotechnologie (INT) und Karlsruher Nano-Micro-Facility (KNMF), Karlsruher Institut für Technologie (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany

Abstract

The hydrido silyl iron complex (o-Ph₂PC₆H₄SiMe₂)Fe(PMe₃)₃H (2) was obtained via the activation of the Si–H bond of the bidentate silyl ligand o-Ph₂P(C₆H₄)SiMe₂H (1) by Fe(PMe₃)₄. 2 showed good to excellent catalytic activity in both the reduction of aldehydes/ketones and the dehydration of benzamide. In addition, with complex 2 as a catalyst, α,β-unsaturated carbonyls could be selectively reduced to the corresponding α,β-unsaturated alcohols. The mechanisms of the formation of 2 and the catalytic dehydration process are proposed and partly experimentally verified.

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Synthesis of silyl iron hydride via Si–H activation and its dual catalytic application in the hydrosilylation of carbonyl compounds and dehydration of benzamides†

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Synthesis of silyl iron hydride via Si–H activation and its dual catalytic application in the hydrosilylation of carbonyl compounds and dehydration of benzamides

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