Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones

Du, Xiaochen; Huang, Jianjun; Nechaev, Anton A.; Yao, Ruwei; Gong, Jing; Eycken, Erik V. Van der; Pereshivko, Olga P.; Peshkov, Vsevolod A.

doi:10.3762/bjoc.14.234

Cited by 15 publications

(9 citation statements)

References 65 publications

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“…A multicomponent Ugi reaction in MeOH or TFE yields propargylamides (Scheme ). A subsequent Au-catalyzed cyclization of this intermediate carried out with varying amounts of AuPPh 3 Cl and AgOTf delivered 2-quinolone products in up to 99% yield. Electron-rich arenes and aliphatic/aryl propargyl amides were used.…”

Section: Cyclization Reactionsmentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

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1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions. The use of this solvent has exponentially increased in the past decade and has become a solvent of choice in some areas, such as C–H functionalization chemistry. In this review, following a brief history of HFIP in organic synthesis and an overview of its physical properties, literature examples of organic reactions using HFIP as a solvent or an additive are presented, emphasizing the effect of solvent of each reaction.

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Section: Cyclization Reactionsmentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

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Section: Six-membered Azacycle Formationmentioning

confidence: 99%

“…Pereshivko and Peshkov's group developed a method to form 2-quinolones with a branching nitrogen substituent (Scheme 27). 44 The approach involves a four-component Ugi reaction followed by intramolecular alkyne hydroarylation catalyzed by gold. The reaction took place in between post-Ugi alkynes 74 , 5–20 mol% AuPPh 3 Cl, 5–20 mol% AgOTf in 2,2,2-trifluoroethanol at room temperature for 6–12 h and gave the desired products 75 in 75–99% yield.…”

Section: Intramolecular Hydroarylation Reactionmentioning

confidence: 99%

Gold-catalyzed hydroarylation reactions: a comprehensive overview

2022

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“…Peshkov and Pereshivko further studied the Au-catalyzed cyclization of alkynyl amides and developed a two steps procedure for the synthesis of quinolones 549 possessing a variety of groups on the nitrogen atom (Scheme 126). 224 The structural diversity was generated during the first step by a Ugi MCR. The use of (Ph 3 P)AuCl/AgOTf (5−20 mol %) as the catalytic system in TFE or HFIP was found optimal.…”

Section: Alkynyl Carbonyl Derivativesmentioning

confidence: 99%

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

et al. 2020

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This review describes the gold-catalyzed reactions of specially activated alkynes, allenes, and alkenes. Such species are characterized by the presence of either electron-donating or electron-withdrawing groups as substituents of the carbon π-system. They are intrinsically polarized, and when compared to their nonspecially activated counterparts can therefore be involved in gold-catalyzed transformations featuring increased regio-, stereo-, and chemoselectivities. The chemistry of specially activated carbon π-systems under homogeneous gold catalysis is extremely rich and varied. The reactivity observed with nonspecially activated unsaturated systems can often be transposed to specially activated ones without loss of efficiency. However, specially activated carbon π-systems also exhibit specific reactivities that cannot be attained with regular substrates. In this family of carbon π-systems, ynamides and their analogs, along with alkynyl carbonyl derivatives, are the classes of substrates that have retained the most attention. This review provides an overview of the chemistry developed with all classes of specially activated carbon π-systems by discussing their general and specific reactivities, presenting and commenting on their gold-catalyzed transformations as well as their applications.

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Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones

Cited by 15 publications

References 65 publications

HFIP in Organic Synthesis

HFIP in Organic Synthesis

Gold-catalyzed hydroarylation reactions: a comprehensive overview

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

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