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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.