87180-57-2Relevant academic research and scientific papers
Initiator-dependent chemoselective addition of THF radical to aldehyde and aldimine and its application to a three-component reaction
Yamada, Ken-Ichi,Yamamoto, Yasutomo,Tomioka, Kiyoshi
, p. 1797 - 1799 (2003)
(Matrix presented) The product distribution of the three-component reaction of aldehydes, arylamines, and THF was dependent on a radical initiator, preferentially giving the corresponding THF adducts of imines with dimethylzinc and adducts of aldehyde wit
Direct Metal-Free C–H Functionalization of Cyclic Ethers with Schiff Bases Through an Azobisisobutyronitrile-Initiated Radical Chain Process
Zeng, Haipeng,Lu, Dengfu,Gong, Yuefa
, p. 7231 - 7237 (2017)
The radical-initiated C–H bond functionalization of cyclic ethers with imines represents an efficient way to form C–C bonds and construct 1,2-amino ethers. Despite being a net redox-neutral process, most examples require excess amounts of radical reagents or oxidants to continuously generate the radical species. Herein, we report an atom-economic protocol for the radical addition of cyclic ethers to imines without the need for any oxidant, metal salt, delicate catalyst, or UV irradiation. In the presence of small amounts of AIBN (2 mol-%), tetrahydrofuran smoothly undergoes the reaction with a variety of imines to afford 1,2-amino ethers in moderate to good yields. Preliminary mechanistic studies suggest that this transformation likely proceeds through a radical chain process with the hydrogen atom abstraction as the rate-determining step.
Reactions of syn- and anti-Benzylideneaniline Radical Anions
Ishida, Akito,Itoh, Hiroshi,Takamuku, Setsuo
, p. 1537 - 1540 (1991)
Reactions of a benzylideneaniline radical anion have been studied by spectral and product analyses, in which successive irradiation of uv-light and ionizing radiation at low temperature have been applied to the production of the unstable syn-radical anion
Radical addition of tetrahydrofuran to imines assisted by tert-butyl hydroperoxide
Vil', Vera A.,Grishin, Sergei S.,Baberkina, Elena P.,Kostyagina, Vera A.,Kovalenko, Alexey E.,Terent'ev, Alexander O.
, (2020)
The TBHP-promoted selective radical addition of tetrahydrofuran to imines resulting in β-amino ethers has been developed. The presented radical method of β-amino ether synthesis is based on initiation by available TBHP and does not require metal catalysis
