Advanced Practical Organic Chemistry

Leonard, John; Lygo, Barry; Procter, Garry

doi:10.1201/b13708

Cited by 96 publications

(64 citation statements)

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“…The results are summarized in Table . The data are averages of at least two independent experiments . The products were fully characterized using 1 H NMR analysis, and the α:γ ratios of the product mixtures were determined using 1 H NMR analysis and also by GC analysis.…”

Section: Resultsmentioning

confidence: 99%

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Reactivity of mixed organozinc and mixed organocopper reagents: 11. Nickel‐catalyzed atom‐economic aryl–allyl coupling of mixed (n‐alkyl)(aryl)zincs

Kalkan

2014

Applied Organom Chemis

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Group selectivity in the allylation of mixed (n-butyl)(phenyl)zinc reagent can be controlled by changing reaction parameters. CuCN-catalyzed allylation in tetrahydrofuran (THF)-hexamethylphosphoric triamide is n-butyl selective and also γ-selective in the presence of MgCl 2 , whereas CuI-catalyzed allylation in THF in the presence of n-Bu 3 P takes place with a n-butyl transfer:phenyl transfer ratio of 23:77 and an α:γ transfer ratio of phenyl of 76:24. NiCl 2 (Ph 3 P) 2 -catalyzed allylation in the presence of LiCl is phenyl selective with an α:γ ratio of 65:35. The reaction of methyl-or n-butyl(aryl)zinc reagents with an allylic electrophile in THF at room temperature in the presence of NiCl 2 (Ph 3 P) 2 catalyst and LiCl as an additive provides an atom-economic alternative to aryl-allyl coupling using diarylzincs.The ratio of GC yields of 6a and 7a. e The ratio of GC yields of 6b and 7b. f Stoichiometric cuprate reagent derived from n-BuPhZn and CuI (or CuCN) was prepared in situ. g X = Cl, Br and SCN. h X = Cl, OAc, OTf and acac. /journal/aoc d The ratio of GC yields of (6a + 7a) and (6b + 7b). e The ratio of GC yields of 6a and 7a. f The ratio of GC yields of 6b and 7b.The ratio of GC yields of (6a + 7a) and (6b + 7b). e The ratio of GC yields of 6a and 7a. f The ratio of GC yields of 6b and 7b.Reactivity of mixed organozinc and mixed organocopper reagents: 11

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Section: Resultsmentioning

confidence: 99%

“…All reactions were carried out in oven‐dried glassware under a positive pressure of nitrogen using standard syringe–septum cap techniques . GC analyses were performed using a Thermo Finnigan gas chromatograph equipped with a ZB‐5 capillary column packed with phenylpolysiloxane using the internal standard technique.…”

Section: Methodsmentioning

confidence: 99%

Reactivity of mixed organozinc and mixed organocopper reagents: 11. Nickel‐catalyzed atom‐economic aryl–allyl coupling of mixed (n‐alkyl)(aryl)zincs

Kalkan

2014

Applied Organom Chemis

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“…Tetrahydrofuran was dried and distilled over sodium/benzophenone ketyl prior to use. 26 Dichloromethane was dried and distilled over calcium hydride. 27 Instrumentation 1 H and 13 C NMR spectra were recorded on a Bruker Ascend 500 spectrometer, with chemical shift values expressed in ppm.…”

Section: Methodsmentioning

confidence: 99%

Designing Branched Deoxybenzoin Polyesters as Polymeric Flame Retardants

Stubbs

Brown

Steele

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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AB2 monomers present opportunities to conduct one‐pot syntheses of highly branched or “hyperbranched” polymers, which are known for their distinct physical and chemical properties relative to linear polymers. This paper describes the synthesis of a deoxybenzoin‐containing AB2 monomer and its use in step‐growth polymerization to prepare branched aromatic polyesters. Highly soluble deoxybenzoin polymers were obtained with degrees of branching reaching 0.36 and estimated molecular weights approaching 20 kDa. The phenolic chain ends of the polymer allowed for post‐polymerization modification by silylation and esterification chemistry. TGA and microscale combustion calorimetry revealed these novel aromatic polyesters to possess the critically important characteristics of flame‐retardant polymers, such as high char yield and low heat release. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1765–1770

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“…All reactions were carried out under nitrogen in well-dried glassware. 76 All chemicals used were of reagent grade or purified according to the literature procedures. GC analyses were carried out using a Thermo Finnigan gas chromatograph equipped with a ZB-5 capillary column packed with phenylpolysiloxane using the internal standard technique.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of some ketones via nano-nickel oxide catalyzed acylation of arylzinc reagents; strategy involving the use of mixed (methyl)(aryl)zincs

2018

Turk J Chem

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Nano-NiO catalyzed acylation of mixed (methyl)(aryl)zincs with aromatic acyl halides in THF at room temperature provides a new facile route for aryl-aroyl coupling. Among NiCl 2 .L 2 and NiCl 2 .L (L = monodentate and bidentate phosphine ligand) catalysts, the lower catalyst loading of NiCl 2 (dppf) may seem attractive; however, nano-NiO, being the lowest cost catalyst, is more favorable for aroylation of (methyl)(aryl)zincs. This procedure also provides a supplement to Cu and Pd catalyzed acylation of diorganozincs.

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Advanced Practical Organic Chemistry

Cited by 96 publications

References 0 publications

Reactivity of mixed organozinc and mixed organocopper reagents: 11. Nickel‐catalyzed atom‐economic aryl–allyl coupling of mixed (n‐alkyl)(aryl)zincs

Reactivity of mixed organozinc and mixed organocopper reagents: 11. Nickel‐catalyzed atom‐economic aryl–allyl coupling of mixed (n‐alkyl)(aryl)zincs

Designing Branched Deoxybenzoin Polyesters as Polymeric Flame Retardants

Synthesis of some ketones via nano-nickel oxide catalyzed acylation of arylzinc reagents; strategy involving the use of mixed (methyl)(aryl)zincs

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