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In this study, three different Ga-containing systems based on GaCl3, Ga2Cl6, or ionic [Ga(L)3][GaCl4]3 (L = methylidenemalonate) complex were screened to elucidate the mechanism, regioselectivity, chemoselectivity, and role of Ga mediator in the reaction between two types of acetylenes (phenylacetylene and but-1-yn-1-ylbenzene) and methylidenemalonates, i.e., the 1,2-zwitterionic precursors that are similar to intermediates derived from donor-acceptor cyclopropanes (DACs). Our DFT calculation results clearly show that the ionic gallium