-Phenethylamine Synthesis via Latent Dual Electrophilicity of N-Pyridinium Aziridines. Academic Article uri icon

abstract

  • -Phenethylamines are widely represented in biologically and pharmacologically active organic small molecules. Here, we introduce N-pyridinium aziridines as latent dual electrophiles for the synthesis of -phenethylamines. Bromide-promoted ring opening generates -halopyridinium amines. Selective Ni-catalyzed C-C cross-coupling between organozinc nucleophiles and the benzylic C-Br electrophile affords a diverse family of -functionalized phenethylaminopyridinium salts, and coupling is stereoconvergent in the presence of chiral ligands. Subsequent Ni-catalyzed reductive N-N bond activation within the b-functionalized phenethylamino-pyridinium salts furnishes the products of formal olefin carboamination. Other reductive N-N cleavage reactions are demonstrated to provide access to free primary amines, alkylated amines, heterocycles, and products derived from N-centered radical chemistry. The developed reaction sequence can be implemented in the context of complex molecules and natural product derivatives. Together, the described results provide a general and modular synthesis of -phenethylamines and significantly expand the utility of N-pyridinium aziridines as linchpins in chemical synthesis.

published proceedings

  • Angew Chem Int Ed Engl

author list (cited authors)

  • Samanta, S., Biswas, P., O'Bannon, B., & Powers, D. C.

complete list of authors

  • Samanta, Samya||Biswas, Promita||O'Bannon, Braeden||Powers, David C

publication date

  • May 2024

publisher