Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity

Aiguabella, Nuria; Arce, E.; Pozo, Carlos del; Riéra, Antoni

doi:10.3390/molecules19021763

Cited by 8 publications

(13 citation statements)

References 23 publications

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“…In another study by Riera and co-workers, they studied the influence of the olefin counterpart on the regioselectivity of the reaction [79]. Two olefins other than norbornadiene were used in this study, namely norbornene and ethylene (Scheme 39).…”

Section: Scheme 38mentioning

confidence: 99%

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Pauson–Khand reaction of fluorinated compounds

Escorihuela¹,

Sedgwick²,

Llobat³

et al. 2020

Beilstein J. Org. Chem.

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The Pauson–Khand reaction (PKR) is one of the key methods for the construction of cyclopentenone derivatives, which can in turn undergo diverse chemical transformations to yield more complex biologically active molecules. Despite the increasing availability of fluorinated building blocks and methodologies to incorporate fluorine in compounds with biological interest, there have been few significant advances focused on the fluoro-Pauson–Khand reaction, both in the inter- and intramolecular versions. Furthermore, the use of vinyl fluorides as olefinic counterparts had been completely overlooked. In this review, we collect the advances both on the stoichiometric and catalytic intermolecular and intramolecular fluoro-Pauson–Khand reaction, with special attention to the PKR of enynes containing a fluoride moiety.

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Section: Scheme 38mentioning

confidence: 99%

“… Effect of the olefin partner in the regioselectivity of the PKR with trifluoromethyl alkynes [ 79 ]. …”

Section: Reviewmentioning

confidence: 99%

Pauson–Khand reaction of fluorinated compounds

Escorihuela¹,

Sedgwick²,

Llobat³

et al. 2020

Beilstein J. Org. Chem.

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“…Therefore, the cobalt complexes of alkynes 207 reacted with ethylene, regioselectively giving 2-(trifluoromethyl)cyclopentenones 208 in moderate yields (Scheme 93). 162 Scheme 93. Reaction of preformed cobalt acetylenic complexes with ethylene.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…Reaction of preformed cobalt acetylenic complexes with ethylene. 162 Ethylene was successfully applied in the synthesis of phytoprostane B 1 precursors 210. The reaction of ethylenic cobalt complexes 209 with ethylene in the presence of NMO and molecular sieves led to cyclopentenones 210 in 67-72% yields (Scheme 94).…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Acetylene and Ethylene: Universal C2 Molecular Units in Cycloaddition Reactions

et al. 2021

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“…247,248 An excellent regiocontrol was obtained for dissymmetrical α,α-difluorinated alkynes, 249 but also of particular interest are trifluoromethyl-substituted alkynes, as in the cobalt complex 130, applied in the PKR (Scheme 71). 250,251…”

Section: Syn Thesismentioning

confidence: 99%

Cobalt-Catalysed Bond Formation Reactions; Part 2

Röse

Hilt

2015

Synthesis

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This review summarises the cobalt-catalysed reactions of the years 2008 through 2014. Covered are addition reactions, such as the hydrogenation of double bonds, the addition of C-H bonds to double and triple bonds, C-H activation reactions, cobalt-catalysed cross-coupling reactions and selected additions of H-B and H-Si bonds to unsaturated starting materials. The cobalt-catalysed cycloadditions range from cyclopropanations, [2+2], Pauson-Khand reactions, [2+2+2], [4+2], [6+2] cycloadditions as well as benzannulations. Also covered are Nicholas reactions, cobalt-catalysed Jacobsen's kinetic resolution of epoxides as well as selected miscellaneous cobalt-catalysed processes mainly for carbon-carbon bond formations. 1 Introduction 2 Addition Reactions 3 Homo-and Cross-Coupling Reactions 4 Jacobsen Kinetic Resolution of Epoxides 5 Nicholas Reactions 6 Cycloaddition Reactions 7 Miscellaneous 8 Conclusion

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Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity

Cited by 8 publications

References 23 publications

Pauson–Khand reaction of fluorinated compounds

Pauson–Khand reaction of fluorinated compounds

Acetylene and Ethylene: Universal C2 Molecular Units in Cycloaddition Reactions

Cobalt-Catalysed Bond Formation Reactions; Part 2

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