TY - JOUR
T1 - Direct Carboxylation of Electron-Rich Heteroarenes Promoted by LiO-tBu with CsF and [18]Crown-6
AU - Shigeno, Masanori
AU - Hanasaka, Kazuya
AU - Sasaki, Keita
AU - Nozawa-Kumada, Kanako
AU - Kondo, Yoshinori
PY - 2019/3/1
Y1 - 2019/3/1
N2 - We herein demonstrate that the combination of LiO-tBu, CsF, and [18]crown-6 efficiently promotes the direct C−H carboxylation of electron-rich heteroarenes (benzothiophene, thiophene, benzofuran, and furan derivatives). A variety of functional groups, including methyl, methoxy, halo, cyano, amide, and keto moieties, are compatible with this system. The reaction proceeds via the formation of a tert-butyl carbonate species.
AB - We herein demonstrate that the combination of LiO-tBu, CsF, and [18]crown-6 efficiently promotes the direct C−H carboxylation of electron-rich heteroarenes (benzothiophene, thiophene, benzofuran, and furan derivatives). A variety of functional groups, including methyl, methoxy, halo, cyano, amide, and keto moieties, are compatible with this system. The reaction proceeds via the formation of a tert-butyl carbonate species.
KW - Brønsted base
KW - C−H functionalization
KW - carbon dioxide
KW - carboxylation
KW - heterocycles
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U2 - 10.1002/chem.201805926
DO - 10.1002/chem.201805926
M3 - Article
C2 - 30637844
AN - SCOPUS:85061194468
VL - 25
SP - 3235
EP - 3239
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 13
ER -