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Gold‐Catalyzed Synthesis of Dibenzopentalenes – Evidence for Gold Vinylidenes
Author(s) -
Hashmi A. Stephen K.,
Wieteck Marcel,
Braun Ingo,
Nösel Pascal,
Jongbloed Linda,
Rudolph Matthias,
Rominger Frank
Publication year - 2012
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.201200086
Subject(s) - chemistry , catalysis , acetylide , aryl , substituent , pentalene , combinatorial chemistry , photochemistry , medicinal chemistry , organic chemistry , molecule , alkyl
A series of easily accessible arene‐1,2‐diynes, bearing one aryl substituent on one of the alkynyl groups, is readily converted to dibenzopentalenes in good yields by gold(I) catalysts. The participation of gold acetylides could be proven by the direct conversion to the corresponding gem ‐diaurated dibenzopentalenes with a gold catalyst. From an experiment with a gold acetylide complex and stoichiometric amounts of the gold “catalyst” the corresponding gem ‐diaurated complex of a dibenzopentalene could be obtained and characterized by X‐ray crystal structure analysis. Labelling studies with deuterated alkynes show the expected deuteration of the two remaining positions of the pentalene core. All this provides evidence for a dual activation mode of the reaction and gold(I) vinylidene complexes as intermediates of the catalytic cycle.