Synthesis and Application of β‐Substituted Pauson–Khand Adducts: Trifluoromethyl as a Removable Steering Group

Aiguabella, Nuria; Pozo, Carlos del; Fustero, Santos; Riéra, Antoni

doi:10.1002/ange.201300907

Cited by 9 publications

(4 citation statements)

References 47 publications

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“…Thus, while in the case of terminal alkynes only the α‐substituted cyclopentenone 68 is formed (Scheme 41A), with internal nonsymmetrical alkynes the final regiochemistry strongly depends on a difficult to predict combination of steric and electronic effects. In this context, Riera, Fustero and co‐workers in 2013 generalized the use of trifluoromethylalkynes 69 as substrates for the PKR [84] . The copper‐catalyzed trifluoromethylation of terminal alkynes described by Qing et al .…”

Section: Cycloaddition Reactionsmentioning

confidence: 99%

“…In this context, Riera, Fustero and co-workers in 2013 generalized the use of trifluoromethylalkynes 69 as substrates for the PKR. [84] The copper-catalyzed trifluoromethylation of terminal alkynes described by Qing et al allowed the efficient preparation of a small library of substrates bearing aryl, alkyl, and alkenyl substituents. [85] These were isolated after complexation with Co 2 (CO) 8 as the corresponding adducts, due to difficulties in their isolation.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

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Fluorinated Imines in Tandem and Cycloaddition Reactions

Escorihuela

Fustero

2023

The Chemical Record

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The chemistry of fluorinated compounds has experienced extraordinary growth in recent decades due to the many and varied properties which many of the compounds that contain fluorinated groups possess. Among all of them, fluorinated chiral imines, in particular the Ellman's imines, are of great importance since they are some of the most interesting building blocks for the synthesis of a large number of enantioenriched carbocycles and heterocycles with extraordinary biological and synthetic properties. This personal account covers the most significant results obtained in our research group in the last two decades concerning asymmetric tandem reactions, paying special attention to the intramolecular aza‐Michael reaction (IMAMR), diversity oriented synthesis (DOS), asymmetric tandem reactions involving a p‐tolylsulfinyl group as chiral inducer and cycloaddition processes, in particular, the Pauson‐Khand reaction, [2+2+2]‐cycloadditions and metathesis reactions, starting mainly from enyne compounds and through the use of fluorinated chiral N‐sulfinyl imines and their derivatives as starting materials.

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Section: Cycloaddition Reactionsmentioning

confidence: 99%

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

Fluorinated Imines in Tandem and Cycloaddition Reactions

Escorihuela

Fustero

2023

The Chemical Record

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“…Then, the following addition of the terminal alkynes afforded the corresponding products at room temperature with similar yields to those reported in their first communication. Note that this method to prepare trifluoromethylated alkynes was applied by Riera and co‐workers in their study toward the synthesis of β‐substituted Pauson–Khand adducts 45…”

Section: Fluorinated Alkynesmentioning

confidence: 99%

“…Note that this method to prepare trifluoromethylated alkynes was applied by Riera and co-workers in their study toward the synthesis of b-substituted Pauson-Khand adducts. [45] Despite the effectiveness of these both aforementioned methods, a stoichiometric amount of copper was still required to complete the transformation. It is therefore unsurprising that Qing and co-workers proceeded to develop a catalytic process (Scheme 27).…”

Section: Introduction Of Cfmentioning

confidence: 99%

Recent Progress in Direct Introduction of Fluorinated Groups on Alkenes and Alkynes by means of CH Bond Functionalization

Besset

Poisson

Pannecoucke

2014

Chemistry A European J

246

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The direct introduction of fluorine and fluorinated building blocks has recently attracted a lot of attention and particularly the direct functionalization of alkenes and alkynes. This review will highlight the major progress recently made in that field, with a focus on photocatalyzed transformations, base-promoted processes, and transition metal-catalyzed functionalization of alkenes and alkynes. Special attention will be paid to explanations of the reaction mechanisms.

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Practical Methods for the Synthesis of Trifluoromethylated Alkynes: Oxidative Trifluoromethylation of Copper Acetylides and Alkynes

et al. 2014

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Two practical and complementary methods are reported for the synthesis of trifluoromethylated alkynes. The first one, a mix-and-stir process, is based on the oxidative trifluoromethylation of readily available and bench-stable copper acetylides while the second one, which displays a broad substrate scope and has several advantages over existing procedures, is based on the oxidative copper-catalyzed direct trifluoromethylation of terminal alkynes. Both reactions provide user-friendly processes for the synthesis of trifluoromethylated acetylenes which can be easily obtained from readily available starting materials.

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Synthesis and Application of β‐Substituted Pauson–Khand Adducts: Trifluoromethyl as a Removable Steering Group

Abstract: Against the rules: The synthesis of the previously unknown β‐substituted regioisomers of the intermolecular Pauson–Khand reaction of terminal alkynes is reported. This regiochemistry was achieved by using the trifluoromethyl group as a removable directing group on the alkyne.

Cited by 9 publications

References 47 publications

Fluorinated Imines in Tandem and Cycloaddition Reactions

Fluorinated Imines in Tandem and Cycloaddition Reactions

Recent Progress in Direct Introduction of Fluorinated Groups on Alkenes and Alkynes by means of CH Bond Functionalization

Practical Methods for the Synthesis of Trifluoromethylated Alkynes: Oxidative Trifluoromethylation of Copper Acetylides and Alkynes

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