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Gold‐Catalyzed Cyclisation by 1,4‐Dioxidation
Author(s) -
Claus Vanessa,
Molinari Lise,
Büllmann Simon,
Thusek Jean,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2019
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.201900996
Subject(s) - iminium , nucleophile , cationic polymerization , catalysis , ketene , chemistry , amide , sulfoxide , nitrogen atom , medicinal chemistry , nitrogen , combinatorial chemistry , photochemistry , organic chemistry , ring (chemistry)
Amide‐substituted diynes were cyclized in the presence of a cationic gold catalyst and an external nucleophile leading to 1‐indenones and 1‐iminoindenones. The electron‐donating features of the nitrogen atom enable the formation of a reactive ketene iminium ion, which can be trapped by either diphenyl sulfoxide or anthranil as nucleophiles in a subsequent oxidation step, providing substituted inden‐1‐on‐3‐carboxamides.