TY - JOUR
T1 - Organic Superbase t-Bu-P4 Catalyzes Amination of Methoxy(hetero)arenes
AU - Shigeno, Masanori
AU - Hayashi, Kazutoshi
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 17K15419 (M.S.), JSPS KAKENHI grant number 19K06967 (M.S.), the Grant for Basic Science Research Projects from The Sumitomo Foundation (M.S.), the Yamaguchi Educational and Scholarship Foundation (M.S.), the 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:
Copyright © 2019 American Chemical Society.
PY - 2019/7/2
Y1 - 2019/7/2
N2 - We report that the organic superbase t-Bu-P4 efficiently catalyzes the amination of methoxy(hetero)arenes with amine nucleophiles such as aniline, indoline, and aminopyridine derivatives. This catalytic reaction is effective for the transformation of electron-deficient methoxyarenes possessing diverse functionalities (carbonyl, cyano, nitro, and halogen) as well as methoxyheteroarenes, including pyrazine, quinoline, isoquinoline, and pyridine derivatives. Intramolecular reactions provide six- and seven-membered ring cyclic amine products.
AB - We report that the organic superbase t-Bu-P4 efficiently catalyzes the amination of methoxy(hetero)arenes with amine nucleophiles such as aniline, indoline, and aminopyridine derivatives. This catalytic reaction is effective for the transformation of electron-deficient methoxyarenes possessing diverse functionalities (carbonyl, cyano, nitro, and halogen) as well as methoxyheteroarenes, including pyrazine, quinoline, isoquinoline, and pyridine derivatives. Intramolecular reactions provide six- and seven-membered ring cyclic amine products.
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U2 - 10.1021/acs.orglett.9b01805
DO - 10.1021/acs.orglett.9b01805
M3 - Article
C2 - 31264886
AN - SCOPUS:85069861005
SN - 1523-7060
VL - 21
SP - 5505
EP - 5508
JO - Organic Letters
JF - Organic Letters
IS - 14
ER -