A Synthetic Route to Sodium α-Aminoalkanesulfinates and Their Application in the Generation of α-Aminoalkyl Radicals for Radical Addition Reactions.

The synthesis of sodium α-aminoalkanesulfinates and their synthetic utility as α-aminoalkyl radical precursors are reported. A variety of α-aminoalkanesulfinates were readily obtained from the reaction between the anions of N-Boc-protected alkylamines and 1,4-diazabicyclo[2.2.2]octanebis(sulfur dioxide). Treatment of sodium α-aminoalkanesulfinates with (diacetoxyiodo)benzene easily generated the corresponding α-aminoalkyl radicals under mild conditions, which were then applied in radical 1,2-addition to imines, radical 1,4-addition to electron-deficient olefins, and radical addition/cyclization to 2-isocyanobiphenyls.