A one-step alternative to the Grignard reaction

Pearce, P. J.; Richards, D. H.; Scilly, N. F.

doi:10.1039/p19720001655

Cited by 69 publications

(26 citation statements)

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“…Bromination of 4- t -butylphenol followed by its alkylation with the desired first ligand L 1 should provide the starting material III . Lithiation of III and subsequent coupling with an aldehyde, IV , 18 carrying L 2 should proceed to give benzylic alcohol, V , which could be reduced with triethylsilane and trifluoroacetic acid to give VI . The challenge is how to repeat this sequence to add the third phenolic moiety.…”

Section: Resultsmentioning

confidence: 99%

“…18 The crude benzylic alcohol obtained from the reaction was reduced with trifluoroacetic acid and triethylsilane 22 to give the tris polyether chelator 11 in 45% yield (two steps) after purification (Scheme 2). A significant biproduct was the reduced monomeric phenol ether.…”

Section: Resultsmentioning

confidence: 99%

“…A solution of aldehyde 15 in anhydrous THF was then added to the aryllithium and the reaction stirred at −78°C for 1 h. 18 After workup and purification, none of the desired coupling product was obtained. The aldehyde 15 was recovered in near quantitative yield along with the debrominated MOM protected phenyl ether, 17 .…”

Section: Resultsmentioning

confidence: 99%

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Synthetic approaches to mixed ligand chelators on tert-butylphenol–formaldehyde oligomer (PFO) platforms

et al. 2012

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Synthetic approaches to mixed ligand chelators on readily available t-butylphenol-formaldehyde oligomer, PFO, scaffolds were examined. In a promising approach, tris and tetraphenol oligomers were selectively mono or di protected using t-butyldiphenyl silyl chloride. The utility of these protected intermediates to prepare representative mixed PFO chelators, carrying ligands such as hydroxamic acid, 3,2-hydroxypyridinones and others was then demonstrated. The introduction of the ligand tethers onto the phenolic scaffold can be done sequentially under relatively mild conditions that tolerate the presence of other sensitive ligand groups. The differential reactivity of the disilyl derivative 20b, allowed stepwise introduction of two different ligands on the internal phenolic positions. This enabled the introduction of three different ligand groups of choice onto the tetra phenol platform.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthetic approaches to mixed ligand chelators on tert-butylphenol–formaldehyde oligomer (PFO) platforms

et al. 2012

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“…Mesitoyl chloride was prepared by treating mesitoic acid with thionyl ch10ride.I~ 2,2-Dimethylpropanal and 2-methyl-4-bromo-2-butene (12) were purchased from Chemical Samples Co. Lithium wire (0.1% Na) was obtained from Ventron and was washed in hexane prior to use. 2-Methyl-2-penten-4-01 (3) was prepared by lithium aluminum hydride reduction of mesityl oxide in dry tetrahydrofuran.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 4-lithio-2-methyl-2-pentene. A new type of allylic organometallic compound

Stanberry¹,

Darmon²,

Fry³

et al. 1976

J. Org. Chem.

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“…A typical reaction protocol is shown in Scheme 8: the cyclopropane 21 is available from aldol condensation of cyclopropylmethylketone with acetone, 25 photooxygenation in polymer beads results in a 62:38 mixture of diastereoisomeric hydroperoxides 22 in 80% yield (combined, only the major isomer shown). Subsequent treatment with 1-20 equivalents of ketone in the presence of catalytic BF 3 afforded the trioxanes 23 in yields of 8-41% (adaman- Scheme 7 Access to 1,2,4-trioxanes by the singlet oxygen route.…”

Section: Peroxyacetalization With Symmetric Ketonesmentioning

confidence: 99%

A Family of New 1,2,4-Trioxanes by Photooxygenation of Allylic Alcohols in Sensitizer-Doped Polymers and Secondary Reactions

Bartoschek¹,

El-Idreesy²,

Griesbeck³

et al. 2005

Synthesis

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Type II photooxygenation (singlet oxygen) is described as a synthetically useful way for the preparation of allylic hydroperoxides and endoperoxides using sensitizer-adsorbed or covalently sensitizer-doped polymeric (macro-or nanosized) containers. Facilitated product separation and purification as well as increased reactivity are advantages of these techniques in comparison with solution-phase photochemistry. The products generated by Type II photooxygenation have been used for the syntheses of numerous polycyclic peroxides with a common 1,2,4-trioxane core as exhibited in the natural antimalarial artemisinin.

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A one-step alternative to the Grignard reaction

Cited by 69 publications

References 0 publications

Synthetic approaches to mixed ligand chelators on tert-butylphenol–formaldehyde oligomer (PFO) platforms

Synthetic approaches to mixed ligand chelators on tert-butylphenol–formaldehyde oligomer (PFO) platforms

Synthesis of 4-lithio-2-methyl-2-pentene. A new type of allylic organometallic compound

A Family of New 1,2,4-Trioxanes by Photooxygenation of Allylic Alcohols in Sensitizer-Doped Polymers and Secondary Reactions

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