879904-83-3Relevant articles and documents
A novel method for preparing silanols from silylmethanols
Takeda, Daisuke,Oyama, Ryo,Yamada, Shozo
supporting information; experimental part, p. 532 - 533 (2011/04/22)
Various types of silylmethanols were converted into their corresponding silanols in good to excellent yield under mild oxidation conditions using TEMPO (2,2,6,6-tetramethyl-l-piperidinyloxyl). Copyright
Palladium-catalyzed cross-coupling of five-membered heterocyclic silanolates
Denmark, Scott E.,Baird, John D.,Regens, Christopher S.
, p. 1440 - 1455 (2008/04/12)
(Chemical Equation Presented) The preparation of π-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Bronsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.
Palladium-catalyzed cross-coupling reactions of heterocyclic silanolates with substituted aryl iodides and bromides
Denmark, Scott E.,Baird, John D.
, p. 793 - 795 (2007/10/03)
Sodium silanolates derived from a number of heterocyclic silanols undergo cross-coupling with a variety of aromatic iodides and bromides under mild conditions. In situ deprotonation of the silanols with an equivalent amount of sodium hydride in toluene ge
