Hydrosilylation of a silicon(II) hydride: synthesis and characterization of a remarkable silylsilylene

Chemistry : a European Journal
Shu-Hua ZhangCheuk-Wai So

Abstract

The synthesis and characterization of novel monomeric silylsilylenes [{PhC(NtBu)(2)}Si--Si{(NtBu)(2)C(H)Ph}R] (R=Cl (2), H (4)) are described. Compound 2 was prepared by the treatment of [{PhC(NtBu)(2)}SiHCl(2)] (1) with two equivalents of potassium graphite, whereas compound 4 was synthesized by the treatment of 1 with four equivalents of potassium graphite. The results suggest that silicon(II) hydride intermediate [{PhC(NtBu)(2)}SiH] was formed in the reduction, which underwent a hydrosilylation with the amidinate ligand of [{PhC(NtBu)(2)}SiR] (R=Cl or H) to form 2 and 4, respectively. The existence of [{PhC(NtBu)(2)}SiH] in solution was demonstrated by the treatment of [{PhC(NtBu)(2)}SiCl] (3) with [K{HB(iBu)(3)}]. Compounds 2 and 4 have been characterized by X-ray crystallography and NMR spectroscopy. The results show that compounds 2 and 4 are stable in solution or the solid state, and do not dimerize to form the corresponding disilene. DFT calculations show that the Si--Si bonds in 2 and 4 do not have multiple-bond character.

References

May 4, 2006·Angewandte Chemie·Cheuk-Wai SoRainer B Oswald
Nov 9, 2006·Journal of the American Chemical Society·Victoria KravchenkoYitzhak Apeloig
Sep 27, 2008·Journal of the American Chemical Society·Takahiro SasamoriNorihiro Tokitoh
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Citations

Oct 28, 2015·Chemical Society Reviews·Carsten Präsang, David Scheschkewitz
May 1, 2012·Angewandte Chemie·Ricardo RodriguezAntoine Baceiredo
Nov 22, 2018·Angewandte Chemie·Martin W StanfordMichael J Cowley
Jul 16, 2013·Chemistry : a European Journal·Hui-Xian YeongCheuk-Wai So
Nov 23, 2011·Angewandte Chemie·Miriam StoelzelMatthias Driess
Dec 20, 2011·Chemical Communications : Chem Comm·S M Ibrahim Al-RafiaEric Rivard
Apr 7, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Anukul JanaDietmar Stalke
Jul 3, 2015·Angewandte Chemie·Priyabrata GhanaAlexander C Filippou
Feb 18, 2011·Chemistry : a European Journal·Shu-Hua ZhangCheuk-Wai So
Jun 8, 2021·Chemical Science·Sebastian KaufmannPeter W Roesky
Aug 28, 2021·Chemical Reviews·Matthew M D RoyEric Rivard

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