Acylsilanes are a fascinating class of compounds that display a number of distinctive chemical and physical properties. The unique reactivity pattern of the acylsilane functional group [R–C(O)Si] makes them an increasingly attractive moiety in modern organic synthesis, and as such, they have been utilised in a diverse range of transformations. This review provides an overview of the recent advances in the synthesis and application of acylsilanes in organic chemistry, with a particular focus on the progress made in the last two decades.

Acylsilanes: valuable organosilicon reagents in organic synthesis

Recent advances in radical transformations of internal alkynes

Geminal bis(silanes) are versatile synthetic building blocks owing to their stability and propensity to undergo a variety of transformations. However, the scarcity of catalytic methods for their synthesis limits their structural diversity and thus their utility for further applications. Herein we report a new method for synthesis of geminal bis(silanes) by means of iron-catalyzed dihydrosilylation of alkynes. Iron catalysts were distinctly superior to the other tested catalysts, which clearly demonstrates that novel reactivity can be found by using iron catalysts. This method features 100% atom economy, regiospecificity, mild reaction conditions, and readily available starting materials. Using this method, we prepared a new type of geminal bis(silane) with secondary silane moieties, the Si–H bonds of which can easily undergo various transformations, facilitating the synthetic applications of these compounds. Preliminary mechanistic studies demonstrated that the reaction proceeds via two iron-catalyzed hyd...

Iron-Catalyzed Dihydrosilylation of Alkynes: Efficient Access to Geminal Bis(silanes)

Cobalt-Catalyzed Asymmetric Synthesis of gem-Bis(silyl)alkanes by Double Hydrosilylation of Aliphatic Terminal Alkynes

The first Pd(0)-catalyzed carbene insertion into Si–Si and Sn–Sn bonds has been realized by using N-tosylhydrazones as the carbene precursors. Geminal bis(silane) and geminal bis(stannane) derivatives were obtained in good to excellent yields under mild conditions. Migratory insertion of Pd carbene is supposed to be the key step for the reaction.

Pd(0)-Catalyzed Carbene Insertion into Si-Si and Sn-Sn Bonds.

Convergent total synthesis of bryostatin 8 has been accomplished by an organosilane-based strategy. The C ring is constructed stereoselectively through a geminal bis(silane)-based [1,5]-Brook rearrangement, and the B ring through geminal bis(silane)-based Prins cyclization, thus efficiently joining the northern and southern parts of the molecule.

Total Synthesis of Bryostatin 8 Using an Organosilane-Based Strategy

Chemoselective deoxygenation of ether-substituted alcohols and carbonyl compounds by B(C6F5)3-catalyzed reduction with (HMe2SiCH2)2

[1,5]-Brook rearrangement: an overlooked but valuable silyl migration to synthesize configurationally defined vinylsilane. The unique steric and electronic effects of geminal bis(silane).

Visible light-promoted radical cyclization of silicon-tethered alkyl iodide and phenyl alkyne. An efficient approach to synthesize benzosilolines

Recent efforts to construct the B-ring of bryostatins.

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