TY - JOUR
T1 - Catalytic Amination of β-(Hetero)arylethyl Ethers by Phosphazene Base t-Bu-P4
AU - Shigeno, Masanori
AU - Nakamura, Ryutaro
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.), 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 - 2019/9/6
Y1 - 2019/9/6
N2 - We describe the catalytic amination of β-(hetero)arylethyl ethers with amines using the organic superbase t-Bu-P4 to obtain β-(hetero)arylethylamines. The reaction has a broad substrate scope and allows the transformations of electron-deficient and electron-neutral β-(hetero)arylethyl ethers with various amines including pyrrole, N-alkylaniline, diphenylamine, aniline, indole, and indoline derivatives. Mechanistic studies indicate a two-reaction pathway of MeOH elimination from the substrate to form a (hetero)arylalkene followed by the hydroamination of the alkene.
AB - We describe the catalytic amination of β-(hetero)arylethyl ethers with amines using the organic superbase t-Bu-P4 to obtain β-(hetero)arylethylamines. The reaction has a broad substrate scope and allows the transformations of electron-deficient and electron-neutral β-(hetero)arylethyl ethers with various amines including pyrrole, N-alkylaniline, diphenylamine, aniline, indole, and indoline derivatives. Mechanistic studies indicate a two-reaction pathway of MeOH elimination from the substrate to form a (hetero)arylalkene followed by the hydroamination of the alkene.
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U2 - 10.1021/acs.orglett.9b02309
DO - 10.1021/acs.orglett.9b02309
M3 - Article
C2 - 31403305
AN - SCOPUS:85071681941
SN - 1523-7060
VL - 21
SP - 6695
EP - 6699
JO - Organic Letters
JF - Organic Letters
IS - 17
ER -