Gold(<scp>i</scp>)-catalysed high-yielding synthesis of indenes by direct C<sub>sp3</sub>–H bond activation

Nahide, Pradip D.; Jiménez‐Halla, J. Óscar C.; Wróbel, Katarzyna; Solorio‐Alvarado, César R.; Ortiz-Alvarado, Rafael; Yahuaca-Juárez, Berenice

doi:10.1039/c8ob02056f

Cited by 42 publications

(16 citation statements)

References 49 publications

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“…Nahide et al developed a gold (I)-catalyzed protocol for the synthesis of indenes 65 through direct CÀ H activation (Scheme 14). [19] For this strategy, variously substituted alkynyl triphenylmethanes 64 (starting materials) were prepared using Pd-catalyzed Sonogashira coupling. The only existing Csp 3 À H bond in the substrate was catalytically activated by gold (I) catalyst 66 (20 mol%) in DCE at 105°C.…”

Section: Gold-catalyzed Coupling Reaction Through Csp 3 à H Activationmentioning

confidence: 99%

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Advances and Prospects in Gold‐Catalyzed C−H Activation

et al. 2020

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The omnipresent character of C−H bonds in organic molecules gives a wide variety of opportunities for the synthesis of a number of functionalized molecules by the activation of the C−H bonds. One of those methods is gold‐catalyzed C−H activation. Recent developments in the area of gold‐catalyzed C−H activation involves annulation reactions leading to the formation of heterocyclic compounds, Au‐catalyzed cross coupling reactions, and C−H functionalization reactions with high atom efficiency. In this short review we summarize the developments and studies carried out in gold‐catalyzed C−H activation over the past decade.

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Section: Gold-catalyzed Coupling Reaction Through Csp 3 à H Activationmentioning

confidence: 99%

“…Nahide et al . developed a gold (I)‐catalyzed protocol for the synthesis of indenes 65 through direct C−H activation (Scheme ) . For this strategy, variously substituted alkynyl triphenylmethanes 64 (starting materials) were prepared using Pd‐catalyzed Sonogashira coupling.…”

Section: Gold‐catalyzed Csp3−h Activation Processesmentioning

confidence: 99%

Advances and Prospects in Gold‐Catalyzed C−H Activation

et al. 2020

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“…Gold is able to activate an alkyne group toward a nucleophilic addition and, for instance, make it susceptible to act as the receptor motif in a hydride shift reaction (Xie et al, 2014; Nahide et al, 2018). In this sense, Wong et al reported the gold-alkyne activation of 1,5-enynes 81 toward a rare 1,6-hydride shift leading to the gold-activated oxonium intermediate 90 , which then experiments a Prins-type cascade forming two new C—C bonds and furnishing the final tricyclic system 91 (Figure 9A) (Lu et al, 2018).…”

Section: Gold-catalyzed Isomerization Processes Involving An Initimentioning

confidence: 99%

Gold-Catalyzed Homogeneous (Cyclo)Isomerization Reactions

2019

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Gold is currently one of the most used metals in organometallic catalysis. The ability of gold to activate unsaturated groups in different modes, together with its tolerance to a wide range of functional groups and reaction conditions, turns gold-based complexes into efficient and highly sought after catalysts. Natural products and relevant compounds with biological and pharmaceutical activity are often characterized by complex molecular structures. (Cyclo)isomerization reactions are often a useful strategy for the generation of this molecular complexity from synthetically accessible reactants. In this review, we collect the most recent contributions in which gold(I)- and/or gold(III)-catalysts mediate intramolecular (cyclo)isomerization transformations of unsaturated species, which commonly feature allene or alkyne motifs, and organize them depending on the substrate and the reaction type.

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“…The synthesis of indenes 71 was achieved under gold(I) catalysis by direct C sp3 –H activation of alkynyl triphenylmethanes 70 that proceeds via a pericyclic [1,5]‐H migration‐cyclization (Scheme ).…”

Section: Transition Metal (Tm)‐catalyzed Processesmentioning

confidence: 99%

Recent Advances in the Synthesis of Indenes

2019

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Indenes constitute an important class of molecules which continue to attract interest from the synthetic organic chemists′ community because not only many natural and synthetic compounds embodying the indene skeleton display bioactivity or pharmaceutical activity but also because indenes find applications in material science, e.g. in photovoltaic solar cells and in the preparation of new fluorescent materials, and in the preparation of metal complexes with special catalytic activity. Many approaches have been exploited in the last four years to build this bicyclic system, the two most explored being cationic processes involving an intramolecular Friedel‐Crafts reaction and those in which a transition metal plays a key role in assembling the indene framework. In this review the results of the synthetic efforts toward indenes made in the 2016–2019 period are reviewed.

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Gold(i)-catalysed high-yielding synthesis of indenes by direct C_sp3–H bond activation

Abstract: A catalytic, practical and high-yielding procedure for the synthesis of indenes by direct Csp3–H activation under gold(i) catalysis was developed.

Cited by 42 publications

References 49 publications

Advances and Prospects in Gold‐Catalyzed C−H Activation

Advances and Prospects in Gold‐Catalyzed C−H Activation

Gold-Catalyzed Homogeneous (Cyclo)Isomerization Reactions

Recent Advances in the Synthesis of Indenes

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Gold(i)-catalysed high-yielding synthesis of indenes by direct Csp3–H bond activation

Abstract: A catalytic, practical and high-yielding procedure for the synthesis of indenes by direct Csp3–H activation under gold(i) catalysis was developed.

Cited by 42 publications

References 49 publications

Advances and Prospects in Gold‐Catalyzed C−H Activation

Advances and Prospects in Gold‐Catalyzed C−H Activation

Gold-Catalyzed Homogeneous (Cyclo)Isomerization Reactions

Recent Advances in the Synthesis of Indenes

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Gold(i)-catalysed high-yielding synthesis of indenes by direct C_sp3–H bond activation