Gold(I)‐Catalyzed Cascade Cyclization Reactions of Allenynes for the Synthesis of Fused Cyclopropanes and Acenaphthenes

Ikeuchi, Takaya; Inuki, Shinsuke; Oishi, Shinya; Ohno, Hiroaki

doi:10.1002/ange.201903384

Cited by 8 publications

(8 citation statements)

References 59 publications

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“…[10] (B) Hashmi ( 2017) Recently, we reported a gold-catalyzed reaction of allenyne 1 to give acenaphthene 2 via the formation of vinyl cation D and carbocyclization with the methyl group (Scheme 2A). [11,12] Based…”

Section: Introductionmentioning

confidence: 99%

Construction of Tricyclic Nitrogen Heterocycles by a Gold(I)‐Catalyzed Cascade Cyclization of Allenynes and Application to Polycyclic π‐Electron Systems

et al. 2021

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An ovel approach to the direct construction of tricyclic nitrogen heterocycles based on gold-catalyzed cascade cyclization of aminoallenynes is described. The expected biscyclization reaction of hydroxyisobutyryl-protected aminoallenynes was efficiently promoted by ac atalytic amount of BrettPhosAuNTf 2 in the presence of iPrOH to produce 1,2dihydrobenzo[cd]indole derivatives in good yields.W hen the reaction was combined with Friedel-Crafts acylation or palladium-catalyzed N-arylation, the resulting tricyclic products were efficiently converted into nitrogen-containing polycyclic aromatic compounds (N-PACs) with highly conjugated p-electron systems.Anewly obtained hexacyclic indolium salt showed characteristic concentration-dependent absorption and emission properties. Scheme 1. Gold(I)-catalyzed reactions of diynes and related compounds proceedingvia vinyl cation intermediates.

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Section: Introductionmentioning

confidence: 99%

Construction of Tricyclic Nitrogen Heterocycles by a Gold(I)‐Catalyzed Cascade Cyclization of Allenynes and Application to Polycyclic π‐Electron Systems

et al. 2021

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“…The most difficult task here would be to determine whether the reaction proceeds via a β‐gold vinyl cation or a gold‐carbene intermediate. [ 135,136 ] It should be noted that the reactivity of both species is complementary, [ 137 ] making it relatively difficult to propose the existence of either by running control experiments. According to quantum‐chemical calculations, direct attack of a water molecule on the ‐gold vinyl cation intermediate C .…”

Section: Functionalization Of Azulene Through Metal‐catalyzed Cross‐c...mentioning

confidence: 99%

“…Alternatively, the cyclopropanation/ring-opening cascade of the β-gold vinyl cation intermediate C would The most difficult task here would be to determine whether the reaction proceeds via a β-gold vinyl cation or a gold-carbene intermediate. [135,136] It should be noted that the reactivity of both species is complementary, [137] Because of the physical and biological significance of azulene derivatives, considerable effort has been expended in developing new and more efficient synthetic techniques. Among these synthetic techniques, transition metal-catalyzed reactions appear to be the most appealing.…”

Section: Cycloizomerization Of Pyridinebridged 18-diynes With Azulenementioning

confidence: 99%

Recent advances in the functionalization of azulene through Rh‐, Ir‐, Ru‐, Au‐, Fe‐, Ni‐, and Cu‐catalyzed reactions

Elwahy

Shaaban

Abdelhamid

2022

Applied Organom Chemis

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Due to their outstanding physicochemical features, azulene derivatives have been proposed for a wide range of prospective technical applications, including molecular switching, sensors, solar cells, and beneficial biological activities. Transition metal‐catalyzed cross‐coupling reactions are catalytic processes that create carbon–carbon bonds in one of the most straightforward and practical ways possible. These techniques have proven to be a very practical way to functionalize azulene. This study summarizes the progress made in this field by employing Rh, Ir, Ru, Au, Fe, Ni, and Cu catalysts over the last two decades.

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“…Commercial reagents were used without further purification after purchase. 2-Bromo-1-iodo-3-methylbenzene (Ikeuchi et al, 2019), 9bromo-9,10-dihydro-9-boraanthracene (Zhou et al, 2012), and 10-bromo-9-oxa-10-boraanthracene (Melaïmi et al, 2006) were prepared according to the literature procedures. Deuterated solvents from Cambridge Isotope Laboratories were used.…”

Section: General Considerationsmentioning

confidence: 99%

Impact of Boron Acceptors on the TADF Properties of Ortho-Donor-Appended Triarylboron Emitters

Mubarok

Lee

et al. 2020

Front. Chem.

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We report the impact of boron acceptors on the thermally activated delayed fluorescence (TADF) properties of ortho -donor-appended triarylboron compounds. Different boryl acceptor moieties, such as 9-boraanthryl ( 1 ), 10 H -phenoxaboryl ( 2 ), and dimesitylboryl (BMes 2 , 3 ) groups have been introduced into an ortho donor (D)–acceptor (A) backbone structure containing a 9,9-diphenylacridine (DPAC) donor. X-ray crystal diffraction and NMR spectroscopy evidence the presence of steric congestion around the boron atom along with a highly twisted D–A structure. A short contact of 2.906 Å between the N and B atoms, which is indicative of an N → B nonbonding electronic interaction, is observed in the crystal structure of 2 . All compounds are highly emissive (PLQYs = 90–99%) and display strong TADF properties in both solution and solid state. The fluorescence bands of cyclic boryl-containing 1 and 2 are substantially blue-shifted compared to that of BMes 2 -containing 3 . In particular, the PL emission bandwidths of 1 and 2 are narrower than that of 3 . High-efficiency TADF-OLEDs are realized using 1 – 3 as emitters. Among them, the devices based on the cyclic boryl emitters exhibit pure blue electroluminescence (EL) and narrower EL bands than the device with 3 . Furthermore, the device fabricated with emitter 1 achieves a high external quantum efficiency of 25.8%.

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Gold(I)‐Catalyzed Cascade Cyclization Reactions of Allenynes for the Synthesis of Fused Cyclopropanes and Acenaphthenes

Cited by 8 publications

References 59 publications

Construction of Tricyclic Nitrogen Heterocycles by a Gold(I)‐Catalyzed Cascade Cyclization of Allenynes and Application to Polycyclic π‐Electron Systems

Construction of Tricyclic Nitrogen Heterocycles by a Gold(I)‐Catalyzed Cascade Cyclization of Allenynes and Application to Polycyclic π‐Electron Systems

Recent advances in the functionalization of azulene through Rh‐, Ir‐, Ru‐, Au‐, Fe‐, Ni‐, and Cu‐catalyzed reactions

Impact of Boron Acceptors on the TADF Properties of Ortho-Donor-Appended Triarylboron Emitters

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