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
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI Grant No. 16H00997 in Precisely Designed Catalysts with Customized Scaffolding (Y.K.), JSPS KAKENHI Grant No. 17K15419 (M.S.), JSPS KAKENHI Grant No. 19K06967 (M.S.), Grand for Basic Science Research Projects from The Sumitomo Foundation (M.S.), Yamaguchi Educational and Scholarship Foundation (M.S.), NIPPON SHOKUBAI Award in Synthetic Organic Chemistry, Japan (M.S.), and also the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED) (M.S., K.N.K., and Y.K.).
Publisher Copyright:
© 2019 American Chemical Society.
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 -