3429-76-3Relevant articles and documents
On the mechanism of the naphthalene-catalysed lithiation: The role of the naphthalene dianion
Yus, Miguel,Herrera, Raquel P,Guijarro, Albert
, p. 3455 - 3458 (2001)
Kinetic and distribution product studies on naphthalene-catalysed lithiation reactions of chlorinated precursors have shown the probable participation of a naphthalene dianion (dilithium naphthalene) as the very active electron carrier agent in the chlorine-lithium exchange process.
Hydrosilane synthesis via catalytic hydrogenolysis of halosilanes using a metal-ligand bifunctional iridium catalyst
Beppu, Teruo,Sakamoto, Kei,Nakajima, Yumiko,Matsumoto, Kazuhiro,Sato, Kazuhiko,Shimada, Shigeru
, p. 75 - 80 (2018/06/20)
Hydrogenolysis of various halosilanes was catalysed by iridium amido complexes to produce hydrosilanes. Selective monohydrogenolysis of di- and trichlorosilanes similarly proceeded, resulting in the formation of chlorohydrosilanes (R2SiHCl or RSiHCl2) as synthetically important building blocks for various organosilicon compounds. A mechanistic study supported the in-situ formation of an iridium hydride species as a key intermediate, which could transfer the hydride to the silicon atom through a metal–ligand bifunctional mechanism. One-pot hydrotrimethylsilylation of olefins was achieved via successive hydrogenolysis and hydrosilylation reactions starting from Me3SiCl.
Utilization of a Trimethylsilyl Group as a Synthetic Equivalent of a Hydroxyl Group via Chemoselective C(sp3)-H Borylation at the Methyl Group on Silicon
Torigoe, Takeru,Ohmura, Toshimichi,Suginome, Michinori
, p. 2943 - 2956 (2017/03/23)
A conversion of trimethylsilylalkanes into the corresponding alcohols is established based on an iridium-catalyzed, chemoselective C(sp3)-H borylation of the methyl group on silicon. The (borylmethyl)silyl group formed by C(sp3)-H borylation is treated with H2O2/NaOH, and the resulting (hydroxymethyl)silyl group is converted into a hydroxyl group by Brook rearrangement, followed by oxidation of the resulting methoxysilyl group under Tamao conditions. An alternative route proceeding through the formylsilyl group formed from a (hydroxymethyl)silyl group by Swern oxidation is also established. The method is applicable to substituted trimethylsilylcycloalkanes and 1,1-dimethyl-1-silacyclopentane for conversion into the corresponding stereodefined cycloalkyl alcohols and 1,4-butanediol.