TY - JOUR
T1 - Deprotonative coupling of pyridines with aldehydes catalyzed by an HMDS-amide base generated in situ
AU - Shigeno, Masanori
AU - Nakaji, Kunihito
AU - Kajima, Akihisa
AU - Nozawa-Kumada, Kanako
AU - Kondo, Yoshinori
N1 - Funding Information:
by JSPS KAKENHI Grant Number 19H03346 (YK), JSPS KAKENHI Grant Number 17K15419 (MS), JSPS KAKENHI Grant Number 19K06967 (MS), Grand for Basic Science Research Projects from The Sumitomo Foundation (MS), Yamaguchi Educational and Scholarship Foundation (MS), NIPPON SHOKUBAI Award in Synthetic Organic Chemistry, Japan (MS), and also the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED) (MS, KNK, and YK).
Publisher Copyright:
© 2019 The Pharmaceutical Society of Japan
PY - 2019
Y1 - 2019
N2 - Herein, the deprotonative functionalization of pyridine derivatives with aldehydes under ambient conditions has been demonstrated using an amide base generated in situ from a catalytic amount of CsF and a stoichiometric amount of tris(trimethylsilyl)amine (N(TMS)3). Pyridine substrates bearing two electron-withdrawing substituents (i.e., fluoro, chloro, bromo, and trifluoromethyl moieties) at the 3- and 5-positions efficiently react at the 4-position with various aldehydes including arylaldehydes, pivalaldehyde, and cyclohexanecarboxaldehyde.
AB - Herein, the deprotonative functionalization of pyridine derivatives with aldehydes under ambient conditions has been demonstrated using an amide base generated in situ from a catalytic amount of CsF and a stoichiometric amount of tris(trimethylsilyl)amine (N(TMS)3). Pyridine substrates bearing two electron-withdrawing substituents (i.e., fluoro, chloro, bromo, and trifluoromethyl moieties) at the 3- and 5-positions efficiently react at the 4-position with various aldehydes including arylaldehydes, pivalaldehyde, and cyclohexanecarboxaldehyde.
KW - Amide base generated in situ
KW - Deprotonative functionalization
KW - Pyridine
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U2 - 10.1248/cpb.c19-00589
DO - 10.1248/cpb.c19-00589
M3 - Article
C2 - 31685747
AN - SCOPUS:85074548642
SN - 0009-2363
VL - 67
SP - 1179
EP - 1182
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 11
ER -