TY - JOUR
T1 - Direct C-2 Carboxylation of 3-Substituted Indoles Using a Combined Brønsted Base Consisting of LiO-tBu/CsF/18-crown-6
AU - Shigeno, Masanori
AU - Tohara, Itsuki
AU - Nozawa-Kumada, Kanako
AU - Kondo, Yoshinori
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI Grant Number 19H03346 (Y. K.), JSPS KAKENHI Grant Number 19K06967 (M. S.), Grant 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.), The Uehara Memorial Foundation (M. S.), and also the Platform Project for Supporting Drug Discovery and Life Science Research funded by the Japan Agency for Medical Research and Development (AMED) (M. S., K. N. K., and Y. K.).
Publisher Copyright:
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2020/4/7
Y1 - 2020/4/7
N2 - Herein, we report that a combination of LiO-tBu, CsF, and 18-crown-6 can be used to carry out the carboxylation of indole derivatives at the C-2 position under an ambient CO2 atmosphere. Substrates bearing an electrophilic substituent (i.e., cyano, formyl, benzoyl, phenylsulfonyl, phenylsulfinyl, and chloride) at the C-3 position are smoothly converted into their corresponding carboxylated products with high functional group compatibility.
AB - Herein, we report that a combination of LiO-tBu, CsF, and 18-crown-6 can be used to carry out the carboxylation of indole derivatives at the C-2 position under an ambient CO2 atmosphere. Substrates bearing an electrophilic substituent (i.e., cyano, formyl, benzoyl, phenylsulfonyl, phenylsulfinyl, and chloride) at the C-3 position are smoothly converted into their corresponding carboxylated products with high functional group compatibility.
KW - Brønsted bases
KW - C1 building blocks
KW - Carbon dioxide fixation
KW - C–H functionalization
KW - Indoles
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U2 - 10.1002/ejoc.202000272
DO - 10.1002/ejoc.202000272
M3 - Article
AN - SCOPUS:85082770411
VL - 2020
SP - 1987
EP - 1991
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 13
ER -