High-Intensity Ultrasound-Promoted Reformatsky Reactions

Ross, Nathan A.; Bartsch, Richard A.

doi:10.1021/jo0261395

Cited by 46 publications

(36 citation statements)

References 16 publications

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“…7,8 In each case, addition of one equivalent of the organozinc reagents occurs with concomitant intramolecular hemiacetal formation, thereby affording 3a (75% yield) and 3b (89% yield), respectively (Scheme 1). Cage dione 1 was first prepared by Cookson and coworkers in 1958.…”

Section: Resultsmentioning

confidence: 99%

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High-intensity ultrasound-promoted Reformatsky reactions of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione

Ross¹,

Bartsch²,

Marchand³

2003

Arkivoc

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Reformatsky reactions of pentacyclo [5.4.0.0 2,6 .0 3,10 .0 5,9 ]undecane-8,11-dione (1) with ethyl bromoacetate and ethyl difluorobromoacetate have been performed in the presence zinc dust and iodine in dioxane under irradiation by high-intensity ultrasound (HIU). In each case, addition of one equivalent of the organozinc reagents occurs with concomitant intramolecular hemiacetal formation, thereby affording 3a (75% yield) and 3b (89% yield), respectively.

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Section: Resultsmentioning

confidence: 99%

“…7,8 A 25-mL, four-armed sonochemical reaction flask capped with rubber septa was flushed with nitrogen for several minutes. Zinc dust (1.18 g,…”

Section: 11-dione (1) Conducted Under Irradiation By High Intensitymentioning

confidence: 99%

High-intensity ultrasound-promoted Reformatsky reactions of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione

Ross¹,

Bartsch²,

Marchand³

2003

Arkivoc

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“…Alkyl phenyl ketones could be transferred to the β-hydroxy esters in a very efficient manner. An advantage of this procedure is also that sterically hindered starting materials could be transferred to their corresponding products (Scheme 19) [75]. The reactions were carried out at 20 kHz (600 W) with a microtip (13 mm).…”

Section: The Refomatsky Reactionmentioning

confidence: 99%

Ultrasound in Synthetic Organic Chemistry

Schmidt¹

2005

Advances in Organic Synthesis

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“…It has been shown recently that high-intensity ultrasound (see Sonication) irradiation of the reaction mixture in presence of I 2 leads to very high yields in short reaction time, without activation of zinc and even using undistilled reagent-grade dioxane. 285 A variety of other low-valent metals (Ba, 286 Mg, Cd, Ni, In, Ce, Li, FeCO 5 ) or metal derivatives such as Cp 2 TiCl, 287 Li[Bu 2 SnI 3 ], 288 SmI 2 , 289,290 can efficiently substitute zinc dust. However, because of their susceptibility to oxidation and hydrolysis these reagents need to be freshly prepared.…”

Section: The Reformatsky Reactionmentioning

confidence: 99%

Zinc: Organometallic ChemistryBased in part on the article Zinc: Organometallic Chemistry by Gerard Parkin which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

Grévy

2005

Encyclopedia of Inorganic and Bioinorganic Chemistry

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Since the discovery of the first organozinc compounds by Sir Edward Frankland in 1849, the organometallic chemistry of zinc made remarkable advances and organozinc species have become essential tools for organic chemists. During the past decade, numerous new and modified procedures for the preparation of the title compounds have been published, rendering their synthesis easier, faster, and less expensive and giving higher yields. The coordination chemistry of organozinc derivatives has been subject of further interest and various intra‐ and intermolecular complexes with different donor ligands have been structurally characterized by X‐ray crystallography and spectroscopic methods. The accumulation of molecular structures, physicochemical studies, and computational calculations has led to a better understanding of the organozinc chemistry, and consequently to the design of new derivatives for specific applications. Even if the development of areas like the chemistry of organozinc anions and cations is still in its early stage, these compounds, which exhibit properties different than those of the parent organometallic species, appear to have promising applications in synthesis and catalytic reactions. During the past ten years, the chemistry of organo‐ gem ‐dizincio derivatives has also been the subject of much interest and progress. These reagents can form two carbon–carbon bonds in a one‐pot reaction and with high stereoselectivity. They became key reagents for organic chemists who want to combine multiple transformations in one operation. The importance of organometallic compounds of zinc can be seen in the growing number of their applications in synthesis. They are used in many reactions such as substitutions, additions to carbonyl compounds and unsaturated systems, cyclopropanations, and polymerizations. Furthermore, as a result of their low reactivity, they tolerate a wide variety of functionalities and perform most of the transformations with high regio‐ and enantioselectivity. After spending more than half a century in the shade of Grignard and organolithium reagents, organozinc reagents are becoming more and more important in modern chemistry.

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High-Intensity Ultrasound-Promoted Reformatsky Reactions

Cited by 46 publications

References 16 publications

High-intensity ultrasound-promoted Reformatsky reactions of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione

High-intensity ultrasound-promoted Reformatsky reactions of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione

Ultrasound in Synthetic Organic Chemistry

Zinc: Organometallic ChemistryBased in part on the article Zinc: Organometallic Chemistry by Gerard Parkin which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

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