A Synthetic Route to Sodium α‑Aminoalkanesulfinates
and Their Application in the Generation of α‑Aminoalkyl
Radicals for Radical Addition Reactions
Posted on 2018-03-23 - 13:16
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.
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Sakamoto, Ryu; Yoshii, Tomomi; Takada, Hiroyuki; Maruoka, Keiji (2018). A Synthetic Route to Sodium α‑Aminoalkanesulfinates
and Their Application in the Generation of α‑Aminoalkyl
Radicals for Radical Addition Reactions. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b00621
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