Abstract
n-Butyllithium (n-BuLi) is one of the most prominent organolithium reagents in the whole of synthetic chemistry,[1] [2] [3] and available as solutions in alkanes such as pentane, hexane, or heptane, which is usually encountered as a pale yellow solution. It is unstable towards air or moisture but stable in an atmosphere of nitrogen. It has been widely used in organic reactions, such as regioselective lithiation reaction,[ 4 ] reversible metathesis reaction,[ 5 ] Claisen rearrangement,[ 6 ] phospho-Fries rearrangement,[ 7 ] coupling reaction,[ 8 ] asymmetric deprotonation–electrophilic trapping reaction,[ 9 ] enantioselective hydroxyalkylation,[ 10 ] etc. In general, n-butyllithium is commercially available and can also be prepared readily by the reaction of 1-bromobutane or 1-chlorobutane with Li metal (Scheme [1]).[ 11 ] An overview of the usage of n-BuLi in organic synthesis is presented below.
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