Air-Stable and Non-Pyrophoric AlMe₃ (DABAL-Me₃)

Bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane Adduct (DABAL-Me₃) is a DABCO-coordinated aluminum reagent. Whereas AlMe₃ is extremely moisture sensitive and has a pyrophoric nature, DABAL-Me₃ is air-stable and non-pyrophoric, which leads to widespread use in organic synthesis as an alternative to AlMe₃. Woodward et al., for example, have reported the cross-methylation of aryl and vinyl halides, using DABAL-Me₃. The reaction proceeds smoothly to afford the corresponding methylated products in high yields.