TY - JOUR
T1 - Modular synthesis of heptaarylindole
AU - Suzuki, Shin
AU - Asako, Takashi
AU - Itami, Kenichiro
AU - Yamaguchi, Junichiro
N1 - Funding Information:
This work was supported by JSPS KAKENHI Grant Number JP18H04272, JP18H04428, JP16H04148 (to J. Y.), the ERATO program from JST (to K. I.), and a JSPS research fellowship for young scientists (to S. S.). We also thanks Dr Yasutomo Segawa and Kenta Kato for assistance with X-ray crystal structure analysis and computational studies. We thank Dr Yoshihiro Ishihara (Vertex Pharmaceuticals) for fruitful discussion and critical comments. ITbM is supported by the World Premier International Research Center (WPI) Initiative, Japan.
Publisher Copyright:
© 2018 The Royal Society of Chemistry.
PY - 2018
Y1 - 2018
N2 - The first synthesis of heptaarylindole (HAI) has been accomplished using a coupling/ring transformation strategy. Four readily prepared modular units (diarylthiophenes, 2-arylaziridines, arylboronic acids, and arylalkynes) were joined together to provide key ynamide intermediates. Subsequent inverse electron-demand intramolecular [4 + 2] cycloaddition furnished pentaarylindoles (PAIs) regioselectively. This strategy was also applied to the synthesis of tetraarylazaindole with four different aryl substituents. PAIs underwent further arylations at the C2- and N1-positions, providing HAI with seven different aryl substituents with virtually complete regioselectivity.
AB - The first synthesis of heptaarylindole (HAI) has been accomplished using a coupling/ring transformation strategy. Four readily prepared modular units (diarylthiophenes, 2-arylaziridines, arylboronic acids, and arylalkynes) were joined together to provide key ynamide intermediates. Subsequent inverse electron-demand intramolecular [4 + 2] cycloaddition furnished pentaarylindoles (PAIs) regioselectively. This strategy was also applied to the synthesis of tetraarylazaindole with four different aryl substituents. PAIs underwent further arylations at the C2- and N1-positions, providing HAI with seven different aryl substituents with virtually complete regioselectivity.
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U2 - 10.1039/c8ob00993g
DO - 10.1039/c8ob00993g
M3 - Article
C2 - 29736544
AN - SCOPUS:85047492652
SN - 1477-0520
VL - 16
SP - 3771
EP - 3776
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 20
ER -