Gallium metal is effective in mediating the allylation of various carbonyl compounds and imines under solvent-free conditions, with the application of sonic energy, affording the corresponding homoallylic alcohols and amines. The imines themselves were also prepared under solventless conditions in high yield, thereby establishing a two-step solvent-free synthesis of homoallylic amines. In comparison, indium metal produced a mixture of the desired homoallylic secondary amine and the bisallylated species via an iminium ion intermediate. (C) 2003 Elsevier Ltd. All rights reserved.
Andrews, P. C., Peatt, A. C., & Raston, C. (2004). Gallium metal mediated allylation of carbonyl compounds and imines under solvent-free conditions. Tetrahedron Letters, 45(2), 243-248. https://doi.org/10.1016/j.tetlet.2003.10.188