Gold‐Catalyzed Cyclisation by 1,4‐Dioxidation | Zendy

Claus Vanessa | Zendy; Molinari Lise | Zendy; Büllmann Simon | Zendy; Thusek Jean | Zendy; Rudolph Matthias | Zendy; Rominger Frank | Zendy; Hashmi A. Stephen K. | Zendy

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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.

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