Michael addition in water using dialkyldithiocarbamate salt as double-chain amphiphilic organocatalyst

Water, a green solvent in organic synthesis, poses challenges due to its high polarity, leading to poor solubility of organic compounds. To address this challenge, employing amphiphiles to create nanoreactors enhances homogeneity and reaction efficiency. Recently, catanionic vesicles generated by combining oppositely charged amphiphiles, have shown promise as alternative nanoreactors. However, their full potential remains unexplored. In this study, we designed novel CatAnionic vesicles derived from N,N-dialkyldithiocarbamates (DTCs), synthesized through a one-step condensation with excellent yields. The DTC amphiphiles in water formed vesicles and catalyzed Michael addition. N,N-didodecylammonium N,N-didodecyldithiocarbamate (AmDTC-C12C12) exhibited the highest reactivity for catalysis of Michael addition to produce 22 Michael adducts with good to high yields. The preparative scale of one-pot Michael addition via an in situ generation of AmDTC-C12C12 was applied to synthesize (±)-baclofen, achieving a yield of 54% over three steps. The AmDTC-C12C12 was successfully reused for seven cycles with consistently high yields. Moreover, the AmDTC-C12C12 was recycled through a chemical recycling process to generate N,N-didodecylammonium chloride, thereby recycling back secondary amine. These findings underscore DTC salts' versatility and efficiency in vesicular catalysis, promising sustainable scalability.