Silylation

[1] Silyl groups are commonly used for: alcohol protection, enolate trapping, gas chromatography, electron-impact mass spectrometry (EI-MS), and coordinating with metal complexes.

The overall reaction scheme is as follows: Other silylating agents include bis(trimethylsilyl)acetamide (BSA).

The reaction of BSA with alcohols gives the corresponding trimethylsilyl ether, together with acetamide as a byproduct (Me = CH3):[4] Due to the strength of the Si-F bond, fluoride salts are commonly used as a deprotecting agent of silyl groups.

To add bulkier alkyl silyls, more strenuous conditions are required for alcohol protection.

[9] In acidic conditions, alkyl substituents acting as electron withdrawing groups decrease the reaction rate.

[8] In basic conditions, alkyl substituents acting as electron donating groups decrease reaction rate.

Metal silyl complexes are intermediates in hydrosilation, a process used to make organosilicon compounds on both laboratory and commercial scales.