Facile Synthesis of Azaspirocycles via Iron Trichloride-Promoted Cyclization/Chlorination of Cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols

Yeh, Ming Chang P.; Fang, Cheng Wei; Lin, Hsin Hui

doi:10.1021/ol300434m

Cited by 27 publications

(9 citation statements)

References 43 publications

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“…[18] The (Z)-4-(arylchloromethylene)-substituted azaspiro [4.6] The research group of Yeh in 2012, reported an intramolecular spirocyclization-chlorination of alkyne-tethered cyclic alcohols under FeCl 3 catalysis (Scheme 16A). [19] This synthetic route provides the access to (Z)-4-(arylchloromethylene)-substituted azaspirocycles 44 and spirocarbocyclic analogues 45 from 46 and 47 respectively, in good to excellent yields. The reaction rates are very high (1 min reaction time) and proceeds even in the presence of air.…”

Section: Cyclizative Coupling Strategiesmentioning

confidence: 96%

Fe‐Catalysed Coupling Reactions Between Alkynes and Alcohols

Khan

Baire

2021

The Chemical Record

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In this review, we discussed about the synthetic developments in the field of Fecatalysis for the formation of -bonds through the coupling of alkynes and alcohols, for the period of 13 years (2008)(2009)(2010)(2011)(2012)(2013)(2014)(2015)(2016)(2017)(2018)(2019)(2020). These strategies fulfil important Green Chemistry principles, as they are highly atom economic (up to 100 %), no toxic by-products (only water), employs highly abundant and low toxic alcohols (no need for any pre-functionalization hence step economy) and cheaper Fe-catalysts. Having these advantages, one can predict that in the coming years a large number of fascinating new iron-catalyzed reactions will be developed for the organic synthesis. We hope that this review article will be highly useful for the synthetic community to design and develop new Fe-catalyzed coupling reactions and keeps the content in the right prospect.

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Section: Cyclizative Coupling Strategiesmentioning

confidence: 96%

Fe‐Catalysed Coupling Reactions Between Alkynes and Alcohols

Khan

Baire

2021

The Chemical Record

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“…Anhydrous iron(III) chloride and its hexa-hydrate feature widely in contemporary organic syntheses, since, because of their Lewis acid properties, they can initiate or catalyze a variety of organic transformations [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ]. Because of their redox properties arising from the 1e − , Fe III /Fe II redox transformation, they are also the basis of a useful polymerization process [ 27 , 28 , 29 , 30 , 31 ], for example the polymerization of thiophene.…”

Section: Iron(iii) and Copper(ii) Chlorides As Chlorination Catalymentioning

confidence: 99%

Metal Fluorides, Metal Chlorides and Halogenated Metal Oxides as Lewis Acidic Heterogeneous Catalysts. Providing Some Context for Nanostructured Metal Fluorides

Lennon

Winfield

2017

Molecules

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Aspects of the chemistry of selected metal fluorides, which are pertinent to their real or potential use as Lewis acidic, heterogeneous catalysts, are reviewed. Particular attention is paid to β-aluminum trifluoride, aluminum chlorofluoride and aluminas γ and η, whose surfaces become partially fluorinated or chlorinated, through pre-treatment with halogenating reagents or during a catalytic reaction. In these cases, direct comparisons with nanostructured metal fluorides are possible. In the second part of the review, attention is directed to iron(III) and copper(II) metal chlorides, whose Lewis acidity and potential redox function have had important catalytic implications in large-scale chlorohydrocarbons chemistry. Recent work, which highlights the complexity of reactions that can occur in the presence of supported copper(II) chloride as an oxychlorination catalyst, is featured. Although direct comparisons with nanostructured fluorides are not currently possible, the work could be relevant to possible future catalytic developments in nanostructured materials.

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“…Another method involved a zinc halides‐catalyzed cycloaddition of propargyl halides with cyclopentadiene, producing the 5‐[aryl(halo)methylene]bicyclo[2.2.1]hept‐2‐enes in low yields 8. Based upon our previous experience with Lewis acid‐promoted carbohalogenations of C‐2 and C‐3 propargyl‐tethered cyclic 2‐enols providing fused9a and spiro bicycles,9b respectively, we anticipated that cyclic 2‐enols bearing a 3‐arylpropargyl tether at the C‐4 position of the ring may alter the reaction path and lead to bridged bicyclic skeletons bearing an exo ‐methylene group. Herein, we describe a Lewis acid‐promoted carbohalogenation of cyclic C‐4‐(3‐aryl‐prop‐2‐ynyl)‐tethered 2‐enols to generate bridged bicyclic compounds having an ( E )‐aryl(halo)methylene group at the C‐5 position.…”

Section: Optimization Of the Reaction Conditions[a]mentioning

confidence: 99%

Convenient Synthesis of (E)‐5‐Aryl(halo)methylenebicyclo‐ [2.2.2]oct‐2‐enes and ‐[2.2.1]hept‐2‐enes via Lewis Acid‐ Promoted Carbohalogenation of Cyclic 2,6‐Enynols

Yeh¹,

Lin²,

Kuo³

et al. 2014

Adv Synth Catal

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An efficient synthesis of (E)-5-aryl(halo)methylenebicyclo[2.2.2]oct-2-enes is reported. Lewis acid-promoted carbohalogenation of 4-(3-arylprop-2-ynyl)-cyclohex-2-enols in dichloromethane proceeds rapidly to afford the exo-methylenebridged bicycles in good yields. This method also provides an easy access to (E)-5-aryl(halo)methyl-A C H T U N G T R E N N U N G enebicyclo[2.2.1]hept-2-enes from the five-membered ring 2,6-enynols. The reactions are procedurally simple and high yielding, producing the aryl(halo)methylene-bridged bicycles in minutes under air and mild conditions.

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Facile Synthesis of Azaspirocycles via Iron Trichloride-Promoted Cyclization/Chlorination of Cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols

Cited by 27 publications

References 43 publications

Fe‐Catalysed Coupling Reactions Between Alkynes and Alcohols

Fe‐Catalysed Coupling Reactions Between Alkynes and Alcohols

Metal Fluorides, Metal Chlorides and Halogenated Metal Oxides as Lewis Acidic Heterogeneous Catalysts. Providing Some Context for Nanostructured Metal Fluorides

Convenient Synthesis of (E)‐5‐Aryl(halo)methylenebicyclo‐ [2.2.2]oct‐2‐enes and ‐[2.2.1]hept‐2‐enes via Lewis Acid‐ Promoted Carbohalogenation of Cyclic 2,6‐Enynols

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