| Summary: | A simple and straightforward addition or defluorination of α-(trifluoromethyl)styrenes with 2-nitroimino-imidazolidine (<b>2a</b>), 2-(nitromethylene)imidazolidine (<b>2b</b>), 2-cyanoimino-thiazolidine (<b>2c</b>), and (<i>E</i>)-1-methyl-2-nitroguanidine (<b>2d</b>), in a controlled manner, was developed. The hydroamination of α-(trifluoromethyl)styrenes with <b>2a</b>, <b>2b</b>, <b>2c</b>, and <b>2d</b> was completed in the presence of DBN at room temperature within 0.5–6 h, affording structurally diverse β-trifluoromethyl-β-arylethyl analogues of neonicotinoids in moderate to good yields. The γ,γ-difluoro-β-arylallyl analogues of neonicotinoids were also successfully synthesized via defluorination of α-(trifluoromethyl)styrenes, with <b>2a</b> and <b>2c</b> using NaH as base at an elevated temperature together with a prolonged reaction time of 12 h. The method features simple reaction setup, mild reaction conditions, broad substrate scope, high functional group compatibility, and easy scalability.
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