Tetrakis(amino)ethylene (TAE)-based reductants are valuable in organic transformations, such as cross-electrophile coupling, but are not widely utilized due to their high cost and complicated syntheses. Here, we report the one-pot synthesis of TAE-derived organic reductants via thermal decomposition of tris(amino)methanes. Specifically, the neat reaction of N,N-dimethylformamide dimethylacetal (DMF-DMA) with pyrrolidine or piperidine generates tetrakis(pyrrolidino)ethylene (TPyE) or tetrakis(piperidino)ethylene (TPiE) in one pot through the in situ generation of a tris(amino)methane intermediate. The synthesis and thermal decomposition of other tris(amino)methanes were also investigated.
Kim et al. (Mon,) studied this question.