Lithium diisopropylamide

Lithium diisopropylamide (commonly abbreviated LDA) is a chemical compound with the molecular formula LiN(CH(CH3)2)2.

It is used as a strong base and has been widely utilized due to its good solubility in non-polar organic solvents and non-nucleophilic nature.

It was first prepared by Hamell and Levine in 1950 along with several other hindered lithium diorganylamides to effect the deprotonation of esters at the α position without attack of the carbonyl group.

As such it is commercially available as a solution in polar aprotic solvents such as THF and ether; however, for small scale use (less than 50 mmol), it is common and more cost effective to prepare LDA in situ.

A weaker base such as an alkoxide, which reversibly deprotonates the substrate, affords the more thermodynamically stable benzylic enolate.

Lithium diisopropylamide
Lithium diisopropylamide
LDA dimer with THF coordinated to Li centers
Deprotonation using LDA. [ 8 ]