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Pd‐Catalyzed Cyclocarbonylation of 2‐(2‐Bromoaryl)indoles with CO as a C1 Source: Selective Access to 6 H ‐Isoindolo[2,1‐ a ]indol‐6‐ones and Indeno[1,2‐ b ]indol‐10(5 H )‐ones
Author(s) -
Guo Shenghai,
Tao Li,
Wang Fang,
Fan Xuesen
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201601067
Subject(s) - regioselectivity , indole test , catalysis , chemistry , reaction conditions , medicinal chemistry , combinatorial chemistry , organic chemistry , stereochemistry
A highly efficient and regioselective synthetic route to 6 H ‐isoindolo[2,1‐ a ]indol‐6‐ones and indeno[1,2‐ b ]indol‐10(5 H )‐ones through the Pd‐catalyzed cyclocarbonylation of 2‐(2‐bromoaryl)indoles under atmospheric CO pressure has been achieved. Notably, the regioselectivity of the reaction was exclusively dependent on the structural characteristics of the indole substrates. With N‐unsubstituted indoles as the starting materials, the reaction afforded 6 H ‐isoindolo[2,1‐ a ]indol‐6‐ones in good‐to‐excellent yields. On the other hand, with N‐substituted indoles as the substrates, the reaction gave indeno[1,2‐ b ]indol‐10(5 H )‐ones in a highly regioselective manner.