TY - JOUR
T1 - Fluorination of Orthothioesters through Oxidative Desulfurization-Fluorination
AU - Furuta, Satoru
AU - Kuroboshi, Manabu
AU - Hiyama, Tamejiro
PY - 1998/8
Y1 - 1998/8
N2 - The oxidative desulfurization-fluorination of orthothioesters of type RCH2C(SMe)3 using n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin gave bromodifluorination products RCHBrCF2SMe in good yields. The products were converted into bromodifluoro olefins RCBr=CF2 via oxidation and thermolysis. In a similar way, the orthothioesters of type RCH(OH)C(SMe)3 or RCH(OAc)C(SMe)3 were fluorinated to afford difluoro ketones RCOCF2SMe or difluoro acetates RCH(OAc)CF2SMe, respectively. The difiuoro acetates were reduced to RCH(OAc)CF2H by radical reduction. The mechanisms are discussed for difluorination accompanied by bromination or oxidation.
AB - The oxidative desulfurization-fluorination of orthothioesters of type RCH2C(SMe)3 using n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin gave bromodifluorination products RCHBrCF2SMe in good yields. The products were converted into bromodifluoro olefins RCBr=CF2 via oxidation and thermolysis. In a similar way, the orthothioesters of type RCH(OH)C(SMe)3 or RCH(OAc)C(SMe)3 were fluorinated to afford difluoro ketones RCOCF2SMe or difluoro acetates RCH(OAc)CF2SMe, respectively. The difiuoro acetates were reduced to RCH(OAc)CF2H by radical reduction. The mechanisms are discussed for difluorination accompanied by bromination or oxidation.
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U2 - 10.1246/bcsj.71.1939
DO - 10.1246/bcsj.71.1939
M3 - Article
AN - SCOPUS:0031869571
SN - 0009-2673
VL - 71
SP - 1939
EP - 1951
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 8
ER -