139747-92-5Relevant academic research and scientific papers
An Electroreductive Approach to Radical Silylation via the Activation of Strong Si-Cl Bond
Lu, Lingxiang,Siu, Juno C.,Lai, Yihuan,Lin, Song
supporting information, p. 21272 - 21278 (2020/12/21)
The construction of C(sp3)-Si bonds is important in synthetic, medicinal, and materials chemistry. In this context, reactions mediated by silyl radicals have become increasingly attractive but methods for accessing these intermediates remain limited. We present a new strategy for silyl radical generation via electroreduction of readily available chlorosilanes. At highly biased potentials, electrochemistry grants access to silyl radicals through energetically uphill reductive cleavage of strong Si-Cl bonds. This strategy proved to be general in various alkene silylation reactions including disilylation, hydrosilylation, and allylic silylation under simple and transition-metal-free conditions.
Preparation of 2-(trimethylsilyl)methyl-2-propen-1-ol derivatives by cobalt catalyzed sp2-sp3 coupling
Riaz, M. Tariq,Pohorilets, Ivanna,Hernandez, Jackson J.,Rios, Jeovanna,Totah, Nancy I.
supporting information, p. 2809 - 2812 (2018/06/15)
A practical, operationally simple preparation of 2-(trimethylsilyl)methyl-2-propen-1-ol derivatives is described. The cobalt catalyzed coupling of a protected vinyl halide with trimethylsilylmethylmagnesium chloride shows excellent functional group tolerance and provides these synthetically useful allyl silanes in good overall yield. By this method, the use of highly concentrated organolithium reagents, complex reaction protocols, and expensive starting materials is avoided.
β-Lactam antifungals. II. Enantiocontrolled synthesis of (2R,5S)-2-hydroxymethyl-1-carbapenam, the carba-analog of a clavam antifungal
Konosu,Furukawa,Hata,Oida
, p. 2813 - 2818 (2007/10/02)
(2R,5S)-2-Hydroxymethyl-1-carbapenam (3), the carba-analog of an antifungal β-lactam (2R,5S)-2-(hydroxymethyl)clavam (1), was synthesized in an enantiocontrolled manner, starting from the coupling reaction of an optically active phthalimido-acetate (3S,4S)-4 and an allylsilane 7, followed by removal of the phthalimido group that was crucial for asymmetric induction. Hydroboration, protecting-group interconversion, and cyclization gave 3 stereoselectively.
