18752-21-1Relevant articles and documents
Silicon Grignard Reagents as Nucleophiles in Transition-Metal-Catalyzed Allylic Substitution
Xue, Weichao,Oestreich, Martin
, p. 233 - 239 (2019/01/04)
A broad range of transition-metal catalysts is shown to promote allylic substitution reactions of allylic electrophiles with silicon Grignard reagents. The procedure was further elaborated for CuI as catalyst. The regioselectively is independent of the leaving group for primary allylic precursors, favoring α over γ. The stereochemical course of this allylic transposition was probed with a cyclic system, and anti -dia-stereoselectivity was obtained.
Hydroaminoalkylation of Allylsilanes and a One-Pot Procedure for the Synthesis of 1,5-Benzoazasilepines
Lühning, Lars H.,Strehl, Julia,Schmidtmann, Marc,Doye, Sven
supporting information, p. 4197 - 4202 (2017/03/31)
Allylsilanes undergo highly regioselective intermolecular alkene hydroaminoalkylation with secondary amines in the presence of a titanium mono(formamidinate) catalyst. Corresponding reactions of a suitable allyl(2-bromophenyl)silane which exclusively deliver the branched hydroaminoalkylation products combined with a subsequent Buchwald–Hartwig amination result in the development of an elegant one-pot procedure for the synthesis of literature-unknown silicon analogues of 1,5-benzodiazepines, the so-called 1,5-benzoazasilepines.
Acceleration of the substitution of silanes with Grignard reagents by using either LiCl or YCl3/MeLi
Hirone, Naoki,Sanjiki, Hiroaki,Tanaka, Ryoichi,Hata, Takeshi,Urabe, Hirokazu
supporting information; experimental part, p. 7762 - 7764 (2010/12/25)
Getting up to speed: Both LiCl and the YCl3/MeLi catalyst system have an acceleration effect upon the substitution of silanes using Grignard reagents (see scheme). The method provides access to benzyl-, allyl-, and arylsilanes in good yields from the starting silanes.
