Oxidative Gold Catalysis Meets Photochemistry – Synthesis of Benzo[<i>a</i>]fluorenones from Diynes

Nösel, Pascal; Moghimi, Setareh; Hendrich, Christoph M.; Haupt, Marten; Rudolph, Matthias; Röminger, Frank; Hashmi, A. Stephen K.

doi:10.1002/adsc.201400969

Cited by 27 publications

(11 citation statements)

References 69 publications

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“…Diynes bearing one terminal and one triarylmethyl-substituted alkyne were converted into benzofluorenone derivatives via a one-pot process involving a gold(I)-catalyzed generation of an α-oxo carbenoid at the terminal alkyne, followed by a photocyclization/oxidation. 426 …”

Section: Oxidative Reactionsmentioning

confidence: 99%

Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity

2015

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Section: Oxidative Reactionsmentioning

confidence: 99%

Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity

2015

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“…165 1,2-Ethynylbenzenes bearing one unsubstituted and one triarylmethyl-substituted alkyne (156a-c) were efficiently converted into substituted benzofluorenones 158a-c through a one-pot reaction involving a gold-catalyzed cyclization to indenones 157a-c followed by a photochemical cyclization/oxidation sequence (Scheme 41). 166…”

Section: Synthesis Of Naphthalenesmentioning

confidence: 99%

(Hetero)aromatics from dienynes, enediynes and enyne–allenes

et al. 2016

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The construction of aromatic rings has become a key objective for organic chemists. While several strategies have been developed for the functionalization of pre-formed aromatic rings, the direct construction of an aromatic core starting from polyunsaturated systems is yet a less explored field. The potential of such reactions in the formation of aromatics increased at a regular pace in the last few years. Nowadays, there are reliable and well-established procedures to prepare polyenic derivatives, such as dienynes, enediynes, enyne-allenes and hetero-analogues. This has stimulated their use in the development of innovative cycloaromatizations. Different examples have recently emerged, suggesting large potential of this strategy in the preparation of (hetero)aromatics. Accordingly, this review highlights the recent advancements in this field and describes the different conditions exploited to trigger the process, including thermal and photochemical activation, as well as the use of transition metal catalysis and the addition of electrophiles/nucleophiles or radical species.

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“…A glance at the products and the starting materials reveals that an 1,2-aryl shift has taken place. A comparable gold-catalyzed aryl rearrangement has already been observed in trityl systems, 32 whereby two alkyne units, one terminal and one internal trityl-substituted alkyne unit, were converted into benzofluorenone derivatives.…”

Section: Paper Synthesismentioning

confidence: 55%

Gold Catalysis of Non-Conjugated Haloacetylenes

Siera¹,

Semleit²,

Kreuzahler³

et al. 2020

Synthesis

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Gold-catalyzed reactions of conjugated haloacetylenes are well known and usually result in the formation of addition or dimerization products. Herein, we report a gold-catalyzed reaction of non-conjugated haloacetylenes, which leads exclusively to the halogenated cyclization products. Remarkable is the gold-catalyzed reaction of tritylhaloacetylenes to haloindene derivatives, as mechanistic studies reveal that an 1,2-aryl shift occurs in the initially formed gold complex. The potential functionalization at the halogen atom and the wide scope of these cyclization reactions make them an attractive method for the construction of cyclic systems.

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Oxidative Gold Catalysis Meets Photochemistry – Synthesis of Benzo[a]fluorenones from Diynes

Cited by 27 publications

References 69 publications

Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity

Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity

(Hetero)aromatics from dienynes, enediynes and enyne–allenes

Gold Catalysis of Non-Conjugated Haloacetylenes

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