Trimethylsilylacetylene
Encyclopedia
Trimethylsilylacetylene is an acetylene
molecule protected
on one end by the trimethylsilyl group. It is popularly used in alkynylations, e.g. the Sonogashira reaction. After desilylation (e.g. with TBAF), the ethynyl group is introduced. Using a protected alkyne, as opposed to acetylene gas, prevents further (undesired) coupling reactions and also has the benefit of being a liquid.
This compound is commercially available. It may also be prepared in a manner similar to other silyl compounds: deprotonation of acetylene
with a Grignard reagent, followed by reaction with trimethylsilyl chloride
.
Acetylene
Acetylene is the chemical compound with the formula C2H2. It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in pure form and thus is usually handled as a solution.As an alkyne, acetylene is unsaturated because...
molecule protected
Protecting group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction...
on one end by the trimethylsilyl group. It is popularly used in alkynylations, e.g. the Sonogashira reaction. After desilylation (e.g. with TBAF), the ethynyl group is introduced. Using a protected alkyne, as opposed to acetylene gas, prevents further (undesired) coupling reactions and also has the benefit of being a liquid.
This compound is commercially available. It may also be prepared in a manner similar to other silyl compounds: deprotonation of acetylene
Acetylene
Acetylene is the chemical compound with the formula C2H2. It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in pure form and thus is usually handled as a solution.As an alkyne, acetylene is unsaturated because...
with a Grignard reagent, followed by reaction with trimethylsilyl chloride
Trimethylsilyl chloride
Trimethylsilyl chloride, also known as chlorotrimethylsilane is a silyl halide, with a variety of different uses in chemistry. It has the formula 3SiCl, and under standard conditions it is a colourless liquid, which is stable in the absence of water...
.