TY - JOUR
T1 - Pentafluorophenyl Esters
T2 - Highly Chemoselective Ketyl Precursors for the Synthesis of α,α-Dideuterio Alcohols Using SmI2 and D2O as a Deuterium Source
AU - Li, Hengzhao
AU - Hou, Yuxia
AU - Liu, Chengwei
AU - Lai, Zemin
AU - Ning, Lei
AU - Szostak, Roman
AU - Szostak, Michal
AU - An, Jie
PY - 2020/2/21
Y1 - 2020/2/21
N2 - We report the first highly chemoselective synthesis of α,α-dideuterio alcohols with exquisite incorporation of deuterium (>98% [D2]) using pentafluorophenyl esters as ketyl radical precursors, SmI2 as a mild reducing agent, and D2O as the deuterium source. This system tolerates a variety of functional groups, offering rapid entry to valuable α,α-dideuterated alcohol building blocks. More generally, this report introduces pentafluorophenyl esters as the most reactive O-ketyl precursors reported to date.
AB - We report the first highly chemoselective synthesis of α,α-dideuterio alcohols with exquisite incorporation of deuterium (>98% [D2]) using pentafluorophenyl esters as ketyl radical precursors, SmI2 as a mild reducing agent, and D2O as the deuterium source. This system tolerates a variety of functional groups, offering rapid entry to valuable α,α-dideuterated alcohol building blocks. More generally, this report introduces pentafluorophenyl esters as the most reactive O-ketyl precursors reported to date.
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U2 - 10.1021/acs.orglett.9b04383
DO - 10.1021/acs.orglett.9b04383
M3 - Article
C2 - 31913049
AN - SCOPUS:85078338150
VL - 22
SP - 1249
EP - 1253
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 4
ER -