Heterobimetallic Catalysis: Platinum‐Gold‐Catalyzed Tandem Cyclization/C−X Coupling Reaction of (Hetero)Arylallenes with Nucleophiles

Alonso, José M.; Muñoz, María Paz

doi:10.1002/ange.201800670

Cited by 11 publications

(1 citation statement)

References 59 publications

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“…In 2016, the Nevado group 14 developed an Au/Pd co-catalyzed process involving two independent catalytic cycles connected by transmetalation. Very recently, Munoz's group 15 demonstrated the concept of Au/Pt bimetallic catalysis in concise synthesis of multiheteroarenes.…”

Section: ■ Introductionmentioning

confidence: 99%

Cooperative Au/Ag Dual-Catalyzed Cross-Dehydrogenative Biaryl Coupling: Reaction Development and Mechanistic Insight

et al. 2019

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An operationally simple and highly selective Au/Ag bimetallic-catalyzed cross-dehydrogenative biaryl coupling between pyrazoles and fluoroarenes has been developed. With this reaction, a wide range of biheteroaryl products can be obtained in moderate to good yields with excellent functional group compatibility. The exact role of silver salts, previously overlooked in most gold-catalyzed transformations, has been carefully investigated in this biaryl coupling. Insightful experimental and theoretical studies indicate that silver acetate is the actual catalyst for C–H activation of electron-poor arenes, rather than the previously reported gold(I)-catalyzed process. An unprecedented Au/Ag dual catalysis is proposed, in which silver(I) is responsible for the activation of electron-poor fluoroarenes via a concerted metalation–deprotonation pathway, and gold(III) is responsible for the activation of electron-rich pyrazoles via an electrophilic aromatic substitution process. Kinetic studies reveal that ArFnAu(III)-mediated C–H activation of pyrazoles is most likely the rate-limiting step.

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Section: ■ Introductionmentioning

confidence: 99%

Cooperative Au/Ag Dual-Catalyzed Cross-Dehydrogenative Biaryl Coupling: Reaction Development and Mechanistic Insight

et al. 2019

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Reaction of Indole‐2‐Carboxylates/Carboxylic Acids with Propargylic Alcohols: Dearomative Ring Expansion/Spirocyclization vs Fused Pentacyclics

2021

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Dearomative ring expansion/spirocyclization of indole‐2‐carboxylates with propargylic alcohols bearing electron‐withdrawing aromatic groups in the presence of PTSA leading to spiro[benzo[b]oxazine‐furans] via oxygen insertion along with dihydrocyclopenta[e]indole‐2‐carboxylates is developed; the same reactants under moderately high temperatures, afford fused pyrano‐indolones. In contrast, copper(II) catalyzed annulation of indole‐2‐carboxylic acids with propargylic alcohols at room temperature provides rapid access to a different class of pentacyclic indene fused pyrano‐indolones.

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Duale Gold/Silber‐Katalyse über oxidative Addition zu Alkinylgold(III)‐Zwischenstufen und silberkatalysierte C‐H‐Aktivierung für die direkte Alkinylierung von Cyclopropenen

et al. 2019

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Während goldkatalysierte synergistische katalytische Prozesse,d ie Transmetallierung mit anderen Metallen einbeziehen, gut verstanden sind, sind Au I /Au III -Zyklen in diesen Reaktionen sehr selten. Hier wird eine goldkatalysierte direkte Alkinylierung von Cyclopropenen über zwei aktive Katalysezyklen ermçglicht, ein oxidativer Katalysezyklus mit einem über oxidative Addition gebildeten Alkinyl-Au III -Komplex, und eine silbervermittelte C-H-Aktivierung. Schema 1. Bereits bekannte Au/M-bimetallische Katalyse und die hier neu vorgestellte Au/Ag-bimetallische Katalyse.

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Heterobimetallic Catalysis: Platinum‐Gold‐Catalyzed Tandem Cyclization/C−X Coupling Reaction of (Hetero)Arylallenes with Nucleophiles

Cited by 11 publications

References 59 publications

Cooperative Au/Ag Dual-Catalyzed Cross-Dehydrogenative Biaryl Coupling: Reaction Development and Mechanistic Insight

Cooperative Au/Ag Dual-Catalyzed Cross-Dehydrogenative Biaryl Coupling: Reaction Development and Mechanistic Insight

Reaction of Indole‐2‐Carboxylates/Carboxylic Acids with Propargylic Alcohols: Dearomative Ring Expansion/Spirocyclization vs Fused Pentacyclics

Duale Gold/Silber‐Katalyse über oxidative Addition zu Alkinylgold(III)‐Zwischenstufen und silberkatalysierte C‐H‐Aktivierung für die direkte Alkinylierung von Cyclopropenen

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