Phosphazene base-promoted functionalization of aryltrimethylsilanes

Abstract

The activation of Ar-Si bonds in aryltrimethylsilane was investigated using a catalytic amount of t-Bu-P4 base and selective functionalizations of aryltrimethylsilanes in the absence of strong electron withdrawing groups on the aromatic rings were accomplished.

Phosphazene Base P4-t-Bu

“…31 Phthalides have been used as precursors for the synthesis of anthraquinones. Peterson Olefination.…”

Phosphazene: Preparation, Reaction and Catalytic Role

“…However, the reaction has been limited to aryltrimethylsilanes with strong electron-withdrawing groups on the aromatic rings. It was found that t Bu-P4 base could be used as an excellent catalyst to activate organosilicon compounds and the selective conversions of aryltrimethylsilanes catalysed by t Bu-P4 base have been investigated [57]. The reaction of 1-trimethylsilylnaphthalene with pivaldehyde in the presence of 20 mol% t Bu-P4 base proceeded smoothly at room temperature to give the alcohol in 91% yield.…”

“…Reactions with other aldehydes have been examined; that with benzaldehyde was found to proceed somewhat slowly at room temperature. Other aryl aldehydes with electron-donating groups were also employed as electrophiles and the reactions proceeded smoothly at room temperature [57] (Table 5.5).…”

“…2-Pyridyltrimethylsilane and 3-pyridyltrimethylsilane reacted smoothly to give the alcohols in 67 and 80%. 2-Thienyltrimethylsilane also reacted to give the alcohol in 81% yield [57] (Table 5.6).…”

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

“…In connection with our recent study on the selective transformation of arylsilanes, [3] we investigated the selective silylation of aryl halides with various functional groups catalysed by palladium.…”