“…Thus, we depict here the differentiated reactivities of vinyl carbene derived from cyclopropene with zinc or rhodium complexes as promoters (Figure 1C). For the zinc halide-promoted reaction, the generated ambiphilic zinc carbenoid (Pasco et al., 2013, Nishimura et al., 2015), which is the key intermediate in the Simmons-Smith (SS) reaction (Denmark et al., 1991, Denmark et al., 1992), shows a nucleophilic character and undergoes nucleophilic attack to isatins without elimination of the halogen atom, delivering oxindole derivatives 3 containing a synthetically valuable alkenyl halide moiety. Importantly, despite the theoretical nucleophilicity, the nucleophilic reactivity of the zinc carbenoid without elimination of halogen atoms has never been achieved (Knochel et al., 1989, Retherford et al., 1989), which provides unique access to alkenyl halides using inexpensive and non-toxic zinc halides as halogenating agents under very mild conditions.…”