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Dual Gold(I)‐catalyzed Cyclization of Dialkynyl Pyridinium Salts
Author(s) -
Tšupova Svetlana,
Cadu Alban,
Stuck Fabian,
Rominger Frank,
Rudolph Matthias,
Samec Joseph S. M.,
Hashmi A. Stephen K.
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201700018
Subject(s) - cycloisomerization , pyridinium , hexafluorophosphate , catalysis , alkyl , chemistry , medicinal chemistry , organic chemistry , combinatorial chemistry , polymer chemistry , ionic liquid
Novel dialkynyl pyridines were synthesized and protected as alkyl salts for dual gold(I)‐catalyzed cycloisomerization. Different alkyl groups and counter ions were screened for the salts, with benzyl and hexafluorophosphate providing the best results. The cyclization led to NMR yields of >95 % being obtained for a number of substrates. Step‐wise hydrogenation of products could be performed in one‐pot by Pd/C, with selective reduction of the double bonds, followed by deprotection of the benzyl group.