The synthesis of pyrroles and oxazoles based on gold α-imino carbene complexes

Gold complex [AuCl(NHC)] (NHC=N,N0-dipropylbenzimidazolin-2-ylidene) 1 undergoes facile substitution reactions at the gold(I) center. Treatment of 1 with anionic phenylacetylide or thiophenolate led to the neutral gold complexes 2 and 3, respectively. The cationic gold complexes [Au(NHC)(pyridine)](BF4) [4]BF4 and [Au2(NHC)2(4,4'-bipyridine)](BF4)2 [5](BF4)2 were obtained via abstraction of the chloro ligand from 1 and reaction with the appropriate amine. Reaction of 1 with AgBF4 in the presence of PPh3 instead of an amine led to an inseparable product mixture of the mixed NHC=PPh3 complex [6]BF4, the dicarbene complex [Au(NHC)2]BF4, [7]BF4, and [Au(PPh3)2]BF4, [8]BF4. Crystals of 2 and [6]BF4 were obtained, and X-ray diffraction structure analyses revealed that the gold(I) atoms are coordinated in a linear fashion by the NHC and the co-ligand

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Gold carbenes, gold-stabilized carbocations, and cationic intermediates relevant to gold-catalysed enyne cycloaddition

Chemical Society Reviews ◽

10.1039/c6cs00171h ◽

2016 ◽

Vol 45 (16) ◽

pp. 4533-4551 ◽

Cited By ~ 149

Author(s):

R. J. Harris ◽

R. A. Widenhoefer

Keyword(s):

Direct Detection ◽

Carbene Complexes ◽

Recent Advances ◽

Made In ◽

Cationic Gold

This review highlights recent advances made in the synthesis of cationic gold carbene complexes and in the direct detection of cationic intermediates generated via gold-catalysed enyne cycloaddition.

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Tin- and Germanium-Substituted Enol Ethers from Fischer Carbene Complexes and Group 14 Vinyl Derivatives

Organometallics ◽

10.1021/om9703999 ◽

1997 ◽

Vol 16 (21) ◽

pp. 4525-4526 ◽

Cited By ~ 4

Author(s):

José Barluenga ◽

Rosario González ◽

Francisco J. Fañanás

Keyword(s):

Group 14 ◽

Fischer Carbene Complexes ◽

Enol Ethers ◽

Carbene Complexes ◽

Fischer Carbene ◽

Vinyl Derivatives

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ChemInform Abstract: Anion-Induced Enantioselective Cyclization of Diynamides to Pyrrolidines Catalyzed by Cationic Gold Complexes.

ChemInform ◽

10.1002/chin.201312097 ◽

2013 ◽

Vol 44 (12) ◽

pp. no-no

Author(s):

Asmaa Kamal Mourad ◽

Juliane Leutzow ◽

Constantin Czekelius

Keyword(s):

Gold Complexes ◽

Cationic Gold

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Catalytic domino amination and oxidative coupling of gold acetylides and isolation of key vinylene digold intermediates as a new class of ditopic N-heterocyclic carbene complexes

Chemical Communications ◽

10.1039/c7cc06069f ◽

2017 ◽

Vol 53 (78) ◽

pp. 10835-10838 ◽

Cited By ~ 9

Author(s):

Haifeng Chen ◽

Jiwei Wang ◽

Zejun Hu ◽

Sheng Xu ◽

Min Shi ◽

...

Keyword(s):

Oxidative Coupling ◽

Gold Complexes ◽

Carbene Complexes ◽

New Class

A catalytic domino amination and oxidative coupling of in situ prepared gold acetylides has been developed for the synthesis of abnormal NHC (aNHC) gold complexes, and key vinylene digold intermediates are isolated.

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