879904-85-5Relevant articles and documents
Palladium-catalyzed cross-coupling reactions of heterocyclic silanolates with substituted aryl iodides and bromides
Denmark, Scott E.,Baird, John D.
, p. 793 - 795 (2006)
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
TRI-(ADAMANTYL)PHOSPHINES AND APPLICATIONS THEREOF
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Page/Page column 26, (2017/05/17)
In one aspect, phosphine compounds comprising three adamantyl moieties (PAd3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.
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.