784161-65-5Relevant academic research and scientific papers
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 2-indolyldimethylsilanols with substituted aryl halides
Denmark, Scott E.,Baird, John D.
, p. 3649 - 3652 (2007/10/03)
(Chemical Equation Presented) A mild and general cross-coupling reaction of 2-indolylsilanols has been developed. The experimental variables that lead to successful coupling are (1) the use of sodium terf-butoxide as the activator, (2) the use of copper(l) iodide in stoichiometric quantities, and (3) the use of Pd2-(dba)3·CHCl3 as the catalyst. Under these conditions N-(Boc)-2-indolyldimethylsilanol reacts with a variety of aromatic iodides to afford the coupling products in good yield (70-84%).
