Dual Gold(I)‐catalyzed Cyclization of Dialkynyl Pyridinium Salts

Tšupova, Svetlana; Cadu, Alban; Stuck, Fabian; Röminger, Frank; Rudolph, Matthias; Samec, Joseph S. M.; Hashmi, A. Stephen K.

doi:10.1002/cctc.201700018

Cited by 12 publications

(7 citation statements)

References 88 publications

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“…(2)). [286] The diyne cyclization by dual catalysis has focused so far on the CÀ H insertion of substituents at the alkyne terminus. However, a report by Ohno, Fujii and Hashmi described the CÀ H insertion of gold vinylidenes 350 through substituents in the tether of 351 via σ,π-propyne gold acetylide catalysis, leading to the synthesis of an array of polycyclic fused products (Scheme 63).…”

Section: Hydroarylation Of Enyne and Diyne Surrogatesmentioning

confidence: 99%

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Catalytic Gold Chemistry: From Simple Salts to Complexes for Regioselective C−H Bond Functionalization

Praveen

Dupeux

Michelet

2021

Chemistry A European J

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Gold coordinated to neutral phosphines (R 3 P), Nheterocyclic carbenes (NHCs) or anionic ligands is catalytically active in functionalizing various CÀ H bonds with high selectivity. The sterics/electronic nature of the studied CÀ H bond, oxidation state of gold and stereoelectronic capacity of the coordinated auxiliary ligand are some of the associated selectivity factors in gold-catalyzed CÀ H bond functionalization reactions. Hence, in this review a comprehensive update about the action of different types of gold catalysts, from simple to sophisticated ones, on CÀ H bond reactions and their regiochemical outcome is disclosed. This review also highlights the catalytic applications of Au(I)-and Au(III)species in creating new opportunities for the regio-and siteselective activation of challenging CÀ H bonds. Finally, it also intends to stress the potential applications in selective CÀ H bond activation associated with a variety of heterocycles recently described in the literature.

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Section: Hydroarylation Of Enyne and Diyne Surrogatesmentioning

confidence: 99%

“…Likewise, a series of dialkynyl pyridinium salts 348 under dual activation catalysis by [IPrAu(I)] + species reacted via a cascade sequence of 5‐ endo cyclization/Csp 3 −H activation to generate dihydropentalenopyridinium salts 349 (Scheme 62, Eq. (2)) [286] …”

Section: Hydroarylation Of Enyne and Diyne Surrogatesmentioning

confidence: 99%

Catalytic Gold Chemistry: From Simple Salts to Complexes for Regioselective C−H Bond Functionalization

Praveen

Dupeux

Michelet

2021

Chemistry A European J

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“…352 In addition to o-dialkynylbenzenes, 1,2-bisethynyl-pyridine and -thiophene were shown to be viable substrates. 353,354 The cyclization under dual-gold catalysis can also be practiced with diynes containing a nonarene tether. Diyne 731, prepared by Ugi four-component coupling, undergoes double cyclization under gold catalysis to provide bicyclic pyridone 732 (Scheme 148).…”

Section: Hydrogen Transfermentioning

confidence: 99%

Transition Metal Vinylidene- and Allenylidene-Mediated Catalysis in Organic Synthesis

2019

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With their mechanistic novelty and various modalities of reactivity, transition metal unsaturated carbene (alkenylidene) complexes have emerged as versatile intermediates for new reaction discovery. In particular, the past decade has witnessed remarkable advances in the chemistry of metal vinylidenes and allenylidenes, leading to the evolution of a diverse array of new catalytic transformations that are mechanistically distinct from those developed in the previous two decades. This review aims to provide a survey of the recent achievements in the development of organic reactions that make use of transition metal alkenylidenes as catalytic intermediates and their applications to organic synthesis.

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“…For example, and by analogy with the work performed with aryldiyne substrates, the group of Hashmi developed a procedure for the synthesis of polyclic fused pyridines 80 from pyridinium substrates 77 (Scheme 20). 34 Initial tests showed that the cycloisomerization could not be directly performed from the 'free' pyridines, presumably due to their capacity to strongly bind to gold catalysts. It is also interesting to note that while simple methylpyridium salts exhibit a low to moderate reactivity, the benzyl ones 77 bearing either a…”

Section: Scheme 19mentioning

confidence: 99%

Gold Vinylidenes as Useful Intermediates in Synthetic Organic Chemistry

Gagosz

2019

Synthesis

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Gold vinylidenes have recently emerged as useful intermediates in synthetic organic chemistry. These species, which can principally be accessed by a 1,2-migration process from a gold-activated alkyne or by dual gold catalysis on a diyne substrate, can react with nucleophilic partners or by C–H insertion to produce a variety of functionalized (poly)cyclic compounds. This short review covers the synthetic approaches developed so far to access gold vinylidenes and the different reactivities these species can exhibit.1 Introduction2 1,2-Migration Processes3 Dual Gold Catalysis4 Other Processes5 Conclusion

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Dual Gold(I)‐catalyzed Cyclization of Dialkynyl Pyridinium Salts

Cited by 12 publications

References 88 publications

Catalytic Gold Chemistry: From Simple Salts to Complexes for Regioselective C−H Bond Functionalization

Catalytic Gold Chemistry: From Simple Salts to Complexes for Regioselective C−H Bond Functionalization

Transition Metal Vinylidene- and Allenylidene-Mediated Catalysis in Organic Synthesis

Gold Vinylidenes as Useful Intermediates in Synthetic Organic Chemistry

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