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Access to Indole‐Fused Benzannulated Medium‐Sized Rings through a Gold(I)‐Catalyzed Cascade Cyclization of Azido‐Alkynes
Author(s) -
Greiner Luca C.,
Inuki Shinsuke,
Arichi Norihito,
Oishi Shinya,
Suzuki Rikito,
Iwai Tomohiro,
Sawamura Masaya,
Hashmi A. Stephen K.,
Ohno Hiroaki
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202101824
Subject(s) - indole test , carbene , combinatorial chemistry , chemistry , ring (chemistry) , aryl , ligand (biochemistry) , stereochemistry , catalysis , organic chemistry , receptor , biochemistry , alkyl
Because benzannulated and indole‐fused medium‐sized rings are found in many bioactive compounds, combining these fragments might lead to unexplored areas of biologically relevant and uncovered chemical space. Herein is shown that α‐imino gold carbene chemistry can play an important role in solving the difficulty in the formation of medium‐sized rings. Namely, phenylene‐tethered azido‐alkynes undergo arylative cyclization through the formation of a gold carbene intermediate to afford benzannulated indole‐fused medium‐sized tetracycles. The reactions allow a range of different aryl substitution patterns and efficient access to these otherwise difficult‐to‐obtain medium‐sized rings. This study also demonstrates the feasibility of the semihollow‐shaped C‐dtbm ligand for the construction of a nine‐membered ring.