TY - JOUR
T1 - Double-Carboxylation of Two C-H Bonds in 2-Alkylheteroarenes Using LiO- t-Bu/CsF
AU - Shigeno, Masanori
AU - Sasaki, Keita
AU - Nozawa-Kumada, Kanako
AU - Kondo, Yoshinori
PY - 2019/6/21
Y1 - 2019/6/21
N2 - We describe the double-carboxylation of two C-H bonds (i.e., at the benzylic and the β-positions) in 2-alkylheteroarenes using a combination of LiO-t-Bu and CsF. A diverse range of substrates, namely benzothiophene, thiophene, benzofuran, furan, and indole derivatives, are efficiently converted into the doubly carboxylated products. A variety of functionalities (i.e., methyl, methoxy, halogen, cyano, ester, ketone, and amide moieties) are well tolerated.
AB - We describe the double-carboxylation of two C-H bonds (i.e., at the benzylic and the β-positions) in 2-alkylheteroarenes using a combination of LiO-t-Bu and CsF. A diverse range of substrates, namely benzothiophene, thiophene, benzofuran, furan, and indole derivatives, are efficiently converted into the doubly carboxylated products. A variety of functionalities (i.e., methyl, methoxy, halogen, cyano, ester, ketone, and amide moieties) are well tolerated.
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U2 - 10.1021/acs.orglett.9b01386
DO - 10.1021/acs.orglett.9b01386
M3 - Article
C2 - 31150257
AN - SCOPUS:85067650587
VL - 21
SP - 4515
EP - 4519
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 12
ER -