Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water.
Water induces a change in the product of radical multifunctionalization reactions of aliphatic alkenes involving an sp(3) C-H functionalization by an 1,5-hydrogen shift using tert-butyl nitrite and molecular oxygen. The reaction without water, reported previously, gives nitrated γ-lactols, whereas the reaction in the presence of water produces 4-hydroxy-5-nitropentyl nitrate or 4-hydroxy-3-nitropentyl nitrate derivatives.
Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
Daisuke
D
Hirose
Tsuyoshi
T
Taniguchi
C−H oxidation; free radical; nitration; oxygen; radicals; water