TY - JOUR
T1 - Catalytic Deprotonative α-Formylation of Heteroarenes by an Amide Base Generated in Situ from Tetramethylammonium Fluoride and Tris(trimethylsilyl)amine
AU - Shigeno, Masanori
AU - Fujii, Yuki
AU - Kajima, Akihisa
AU - Nozawa-Kumada, Kanako
AU - Kondo, Yoshinori
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI Grant 23105009 in Advanced Molecular Transformations by Organo-catalysis (Y.K.), JSPS KAKENHI Grant 16H00997 in Precisely Designed Catalysts with Customized Scaffolding (Y.K.), JSPS KAKENHI Grant 17K15419 (M.S.), a Grant for Basic Science Research Projects from The Sumitomo 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) (Y.K., M.S., and K.N.-K.).
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2019/4/19
Y1 - 2019/4/19
N2 - Heteroarene formylations in DMF solution proceed in the presence of an amide base catalyst generated in situ from tetramethylammonium fluoride (TMAF) and tris(trimethylsilyl)amine (N(TMS)3). The reaction proceeds at room temperature and has an operationally simple procedure. Various heteroarenes, including benzothiophene, thiophene, benzothiazole, oxazole, and indole derivatives, can be formylated with high functional group tolerance.
AB - Heteroarene formylations in DMF solution proceed in the presence of an amide base catalyst generated in situ from tetramethylammonium fluoride (TMAF) and tris(trimethylsilyl)amine (N(TMS)3). The reaction proceeds at room temperature and has an operationally simple procedure. Various heteroarenes, including benzothiophene, thiophene, benzothiazole, oxazole, and indole derivatives, can be formylated with high functional group tolerance.
KW - amide base catalyst
KW - anions
KW - formylation
KW - heteroarenes
KW - room-temperature deprotonation
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U2 - 10.1021/acs.oprd.8b00247
DO - 10.1021/acs.oprd.8b00247
M3 - Article
AN - SCOPUS:85064671743
SN - 1083-6160
VL - 23
SP - 443
EP - 451
JO - Organic Process Research and Development
JF - Organic Process Research and Development
IS - 4
ER -