Synthesis of Tetrakis-Amino-Ethylene Derived Organic Reductants via Thermal Decomposition of Tris-Aminomethanes

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 TAEderived organic reductants via thermal decomposition of tris-aminomethanes. 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-aminomethane intermediate. The thermal decomposition of other tris-aminomethanes was also investigated.