Tin-free intermolecular addition of primary alkyls to imines via the dimethylzinc-air radical process.
[reaction: see text] A dimethylzinc-air initiator was applied to the generation of primary alkyl radicals from alkyl iodides. The addition of the generated primary alkyl radicals to N-tosylimines was accelerated by the action of boron trifluoride-diethyl etherate and copper(II) triflate to give the corresponding adducts in good yields after 2-3 h. Air oxygen was essential for the reaction to proceed, showing involvement of a radical process in the reaction.
Yamada
Ken-ichi
K
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Japan.
Yamamoto
Yasutomo
Y
Maekawa
Masaru
M
Akindele
Tito
T
Umeki
Hiroyuki
H
Tomioka
Kiyoshi
K