Affiliation:
1. Department of Chemistry Texas A&M University, College Station Texas 77843 United States
Abstract
Abstractβ‐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 β‐phenethylamines. Bromide‐promoted ring opening generates β‐halopyridinium amines. Selective Ni‐catalyzed C−C cross‐coupling between organozinc nucleophiles and the benzylic C−Br electrophile affords a diverse family of β‐functionalized phenethylaminopyridinium salts, and coupling is stereoconvergent in the presence of chiral ligands. Subsequent Ni‐catalyzed reductive N−N bond activation within the β‐functionalized phenethylaminopyridinium 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 β‐phenethylamines and significantly expand the utility of N‐pyridinium aziridines as linchpins in chemical synthesis.
Funder
National Institute of General Medical Sciences
Welch Foundation
Cited by
1 articles.
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