CeCl<sub>3</sub>·7H<sub>2</sub>O−NaI Catalyzed Hydrooxacyclization of Unsaturated 3-Hydroxy Esters

Marotta, Emanuela; Foresti, Elisabetta; Marcelli, Tommaso; Peri, Francesca; Righi, Paolo; Scardovi, Noemi; Rosini, Goffredo

doi:10.1021/ol026955z

Cited by 51 publications

(26 citation statements)

References 20 publications

(11 reference statements)

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“…[4] The use of transition-metal catalysis for selective hydroalkoxylation of unsaturated hydrocarbons [5] has been reported in the cases of CC [6] and activated C=C bonds such as allenes, [7] 1,3-dienes [8] and Michael acceptors. [9] Ce III /NaI, [10] Ru III /Ag I[11] and Au I /Ag I systems, [12] as well as Pt II complexes in the presence of phosphine ligands, [13] have recently been used as catalysts for the intramolecular hydroalkoxylation of unactivated g-and d-hydroxy alkenes to form cyclic ethers.…”

Section: Introductionmentioning

confidence: 99%

Aluminium(III) Trifluoromethanesulfonate as an Efficient Catalyst for the Intramolecular Hydroalkoxylation of Unactivated Olefins: Experimental and Theoretical Approaches

Coulombel

Rajzmann

Pons

et al. 2006

Chemistry A European J

114

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The Al(OTf)(3)-catalyzed cycloisomerization of unactivated unsaturated alcohols was studied from experimental and theoretical points of view. A series of cyclic ethers was obtained in excellent yields and regioselectivities. This catalyst system provides one of the most straightforward routes to cyclic ethers with Markovnikov-type regioselectivity under mild conditions. Theoretical and NMR studies were carried out in order to better determine the mechanism of this reaction. The NMR studies were in agreement with preferential complexation of Al(OTf)(3) to the oxygen atom of the unsaturated alcohol, but did not exclude complexation to the double bond of the alcohol. Theoretical calculations indicated strong acidification of the hydroxyl proton when Al(OTf)(3) was complexed to the alcohol oxygen atom. A plausible catalytic cycle for the Al(OTf)(3)-catalyzed intramolecular hydroalkoxylation of unactivated olefins is proposed.

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Section: Introductionmentioning

confidence: 99%

Aluminium(III) Trifluoromethanesulfonate as an Efficient Catalyst for the Intramolecular Hydroalkoxylation of Unactivated Olefins: Experimental and Theoretical Approaches

Coulombel

Rajzmann

Pons

et al. 2006

Chemistry A European J

114

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“…CeCl 3 is a very useful metal catalyst, whose unique behavior is used to synthesis various heterocycle. 1a, [17][18][19][20][21] Table 1). 22,23 Various functional groups on the aldehyde (2) with OPD (1) is also examine.…”

Section: Introductionmentioning

confidence: 99%

Metal Catalyzed Synthesis of Pentose-Sugar-Based Chiral 2-Substituted-1H-Benzimidazoles

Halder¹

2020

Preprint

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A metal catalyzed synthetic protocol has been developed using Ti(OBu)4-CeCl3 combo catalyst for chemoselective cyclocondensation cumoxidation under mild reaction conditions toward synthesis of a new class of optically pure compounds, 2-(6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-6a,10a-dihydro-1H-anthra[1,2-d] imidazole-6,11-dione. All pentose-sugar-based aldehydes react with varies substituted dimethyl, 4-benzoyl and benzoquinoyl o-aromatic diamines (OAD) to afford desired chiral benzimidazoles with excellent isolated yield (77%-88%). In this suitable method chiral 2-Substituted-1H-Benzimidazoles were syntheses in high yields without using any hazardous chemicals or harmful acids. Normal aromatic aldehyde also reacts with varies o-aromatic diamines (OAD) give rise to known 2-Aryl-1H-benzimidazoles. All the target chiral 2-Substituted-1H-Benzimidazoles were characterized by FT-IR, NMR spectral and HR-MS data and also verified M.P of normal aromatic 2-Substituted-1H-benzimidazoles from literature.

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“…It is also a cheap, non‐toxic and water‐tolerant catalyst. Due to its unique catalytic properties, CeCl 3 ⋅7H 2 O has been intensively studied as catalyst for a plethora of organic transformations such as hydrooxacyclization of unsaturated 3‐hydroxy esters, Michael addition, dihydroxylation of unreactive olefins and Julia olefination of cyclopropyl carbinols . However, the main limitation from economic and environmental points of view is the use in stoichiometric amounts and involvement in secondary reactions.…”

Section: Introductionmentioning

confidence: 99%

Use of an efficient polystyrene‐supported cerium catalyst for one‐pot multicomponent synthesis of spiro‐piperidine derivatives and click reactions in green solvent

Mondal

Ghosh

Das

et al. 2018

Applied Organom Chemis

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One-pot multicomponent reactions are very demanding in synthetic organic chemistry. Here we report a new polystyrene-supported cerium catalyst (PS-Ce-amtp) obtained via an easy two-step procedure, which was thoroughly characterized using various techniques. PS-Ce-amtp catalyses the environmentally benign one-pot multicomponent synthesis of spiro-piperidine derivatives through the reaction of substituted aniline, cyclic active methylene compound and formaldehyde at room temperature. The catalyst also exhibits excellent catalytic activity in one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles via click reaction between in situ generated azides (derived from anilines and amines) and terminal alkynes. The catalyst can be recovered easily after reaction and reused five times without significant loss in its catalytic activity. The advantageous features of this catalyst are atom economy, operational simplicity, short reaction times, easy handling and high recycling efficiency.

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CeCl₃·7H₂O−NaI Catalyzed Hydrooxacyclization of Unsaturated 3-Hydroxy Esters

Cited by 51 publications

References 20 publications

Aluminium(III) Trifluoromethanesulfonate as an Efficient Catalyst for the Intramolecular Hydroalkoxylation of Unactivated Olefins: Experimental and Theoretical Approaches

Aluminium(III) Trifluoromethanesulfonate as an Efficient Catalyst for the Intramolecular Hydroalkoxylation of Unactivated Olefins: Experimental and Theoretical Approaches

Metal Catalyzed Synthesis of Pentose-Sugar-Based Chiral 2-Substituted-1H-Benzimidazoles

Use of an efficient polystyrene‐supported cerium catalyst for one‐pot multicomponent synthesis of spiro‐piperidine derivatives and click reactions in green solvent

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CeCl3·7H2O−NaI Catalyzed Hydrooxacyclization of Unsaturated 3-Hydroxy Esters

Cited by 51 publications

References 20 publications

Aluminium(III) Trifluoromethanesulfonate as an Efficient Catalyst for the Intramolecular Hydroalkoxylation of Unactivated Olefins: Experimental and Theoretical Approaches

Aluminium(III) Trifluoromethanesulfonate as an Efficient Catalyst for the Intramolecular Hydroalkoxylation of Unactivated Olefins: Experimental and Theoretical Approaches

Metal Catalyzed Synthesis of Pentose-Sugar-Based Chiral 2-Substituted-1H-Benzimidazoles

Use of an efficient polystyrene‐supported cerium catalyst for one‐pot multicomponent synthesis of spiro‐piperidine derivatives and click reactions in green solvent

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CeCl₃·7H₂O−NaI Catalyzed Hydrooxacyclization of Unsaturated 3-Hydroxy Esters