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Gold(I)‐catalyzed synthesis of dihydrodibenzoquinolizinium salts
Author(s) -
Marien Niels,
Verniest Guido
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700126
Subject(s) - chemistry , catalysis , aryl , combinatorial chemistry , reaction mechanism , mechanism (biology) , organic chemistry , philosophy , alkyl , epistemology
A gold‐catalyzed cyclization of 1‐alkynyl‐2‐aryl tetrahydroisoquinolines is described for the synthesis of novel dihydrodibenzoquinolizinium salts. The reaction mechanism is likely to involve a 6‐ endo ‐ dig cyclization and subsequent oxidation by air to give a relatively stable arylgold intermediate. This gold species undergoes protodeauration under acidic conditions to afford the title compounds. An NMR study was performed to gain further evidence and insight on the presence of the arylgold intermediate and the reaction mechanism.