Palladium‐Catalyzed Silylation of Electron‐Deficient Aryl Iodides Using Triorganosilane in the Presence of Pyridine and LiCl

Abstract

Palladium-catalysed silylation of aryl iodides with electronwithdrawing groups was efficiently achieved using pyridine and lithium chloride as additives and conducting the reaction at room temperature. Functionalized aryl[2-(hydroxymethyl)-phenyl]dimethylsilanes were also prepared by palladiumcatalysed reaction using THP-protected [2-(hydroxymethyl)-

Recent Advances in Transition-Metal-Catalyzed Silylations of Arenes with Hydrosilanes: C–X Bond Cleavage or C–H Bond Activation­ Synchronized with Si–H Bond Activation

“…In 2008, Iizuka and Kondo reported the palladium-catalyzed silylation of electron-deficient aryl iodides in yields of up to 94% by using a combination of pyridine as the base and lithium chloride (LiCl) as an additive at room temperature in the presence of palladium(II) acetate [Pd(OAc) 2 ] (Scheme 56). 64 Phenyl-substituted hydrosilanes were found to show better selectivities for the silylation rather than the reduction reaction. However, under their conditions, the silylation of electron-rich aryl halides was unsuccessful.…”

Diphenylphosphinite ionic liquid (IL-OPPh2): A solvent and ligand for palladium-catalyzed silylation and dehalogenation reaction of aryl halides with triethylsilane

“…Conversion of aryl halides to aryltrialkylsilane by trialkylsilane has also been reported under rhodium catalyzes [17][18][19]. As part of the recent developments, ionic liquids as green solvents [20,21] have also been considered as potential media for this purpose [22].…”

A mechanistic investigation of the Pd-catalyzed cross-coupling betweenN-tosylhydrazones and aryl halides

“…191 The traditional assembly method has a limited substrate scope as the reagents involved are highly nucleophilic or basic. Other methods have since emerged; [192][193][194][195][196][197][198] Extending from alkenes and carbonyls, this research set out to shed light on the mechanism of TMSCF 3 and catalytic TBAT on weak C-H acids, namely 1,3difluorobenzenes. With a more complete understanding of the mechanism, the conditions can then be tailored to enhance product generation.…”