Palladium-catalyzed C–Si bond formation via denitrative cross-coupling of nitroarenes with hexamethyldisilane

Abstract

The transition-metal-catalyzed cross-coupling of aryl halides with silylation reagents is a powerful strategy for C(sp2)−Si bond formation. However, the need for the tedious preparation of aryl halides makes the reaction...

Facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by KOtBu

“…11,12 In this context, the conversion of C–Si bonds into C–B bonds has been developed through the reaction with boron trihalides (BCl 3 , BBr 3 ). 13 At the outset of this project, no inverse approach from C–B bonds to C–Si bonds had been developed.…”

Pd/NHC catalyzed reduction and coupling of nitroaromatics for the synthesis of diarylamines

“…In addition to serving as precursors for nucleophilic reagents, nitroaromatics also possess unique advantages as electrophilic reagents, drawing attention. [10][11][12][13][14][15][16][17] Employing nitroaromatics instead of halogenated aromatic can circumvent halogenated waste contamination and certain halogenated aromatic compounds are synthesized through multistep reactions, using nitroaromatics as starting materials. 18 In light of the dual roles of nitroaromatics in cross-coupling reactions, we contemplated the introduction of a reducing agent into the Pd/NHC catalytic system previously reported by our group.…”

“…In addition to serving as precursors for nucleophilic reagents, nitroaromatics also possess unique advantages as electrophilic reagents, drawing attention. 10–17 Employing nitroaromatics instead of halogenated aromatic can circumvent halogenated waste contamination and certain halogenated aromatic compounds are synthesized through multistep reactions, using nitroaromatics as starting materials. 18…”

Cross-Electrophile Silylation of Aryl Carboxylic Esters with Hydrochlorosilanes by SiH-Directed and Cr-Catalyzed Couplings

“…Silylation reactions typically use hydrosilanes, ,, disilanes, halosilanes, , silylmetallic, , and silylborane reagents as silicon sources to form Si–C bonds. Considering a retrosynthetic approach, silylation using hydrochlorosilanes as silicon sources, by coupling with both geminal Si–Cl and Si–H bonds, allows sequential incorporation of several substituents into silicon centers, while enabling the formation of substituted organosilanes efficiently (Figure b) .…”