Facile Barton-McCombie deoxygenation of alcohols with tetrabutylammonium peroxydisulfate and formate ion.
[reaction: see text]. A new method for efficient radical deoxygenation of alcohols is described for preparing bulk chemicals avoiding scale-up problems. Treatment of various thiocarbonyl derivatives with (Bu(4)N)(2)S(2)O(8) and HCO(2)Na in DMF afforded the corresponding deoxygenated products in excellent yields. The deoxygenation appears to be initiated by the transfer of a single electron to thiocarbonyl derivatives from CO(2)(*)(-) rather than from SO4(*)(-).
Park
Hee Sock
HS
Center for Molecular Design and Synthesis, Department of Chemistry, KAIST, Daejeon, Republic of Korea.
Lee
Hee Yoon
HY
Kim
Yong Hae
YH