2006
DOI: 10.1002/adsc.200606090
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Catalyzed Reactions of Alkynes in Water

Abstract: This review summarizes the catalytic organic reactions of alkynes in aqueous media. The aqueous version of the alkyne reactions gives new reactivities, is environmentally friendly, and has broard applications in all areas of chemistry and materials science.

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Cited by 123 publications
(48 citation statements)
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References 110 publications
(133 reference statements)
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“…The resulting reaction mixture was heated under reflux for 12 h. After cooling, the reaction mixture was washed by brine and then extracted with CH 2 Cl 2 . The combined organic extracts were dried over anhydrous Na 2 SO 4 , concentrated in vacuum and purified by flash chromatography on silica gel (eluent: petroleum ether-EtOAc, V∶V=10∶ 1) to afford the desired product 3a (yield: 65%).…”
Section: General Proceduresmentioning
confidence: 99%
See 1 more Smart Citation
“…The resulting reaction mixture was heated under reflux for 12 h. After cooling, the reaction mixture was washed by brine and then extracted with CH 2 Cl 2 . The combined organic extracts were dried over anhydrous Na 2 SO 4 , concentrated in vacuum and purified by flash chromatography on silica gel (eluent: petroleum ether-EtOAc, V∶V=10∶ 1) to afford the desired product 3a (yield: 65%).…”
Section: General Proceduresmentioning
confidence: 99%
“…3 Besides the nucleophilic addition of terminal alkynes with various electrophiles, 4 Sonogashira and other coupling reactions of alkynes are the most popular and powerful methods for the introduction of carbon-carbon triple bond. 5 However, generally halide byproducts were produced along with the desired product.…”
Section: Introductionmentioning
confidence: 99%
“…The ''click chemistry'' based on the Huisgen's 1,3 dipolar cycloaddition between an azide and an alkyne function in presence of a copper catalyst [19,20] can be carried out in various media, including water, and can be very efficiently applied to the preparation of linear block copolymers, dendrimers, gels, surface functionalization, as well as to cells and virus modifications in biomolecular engineering. [21][22][23] The azide group is so far introduced by mesylation of the hydroxyl terminus of previously formed polymers followed by its subsequent substitution with sodium azide. [24,25] Indeed, most of the poly(ethylene glycol) (PEG) azidation routes reported in the literature involve so far the chemical modification of previously formed hydroxyl-terminated PEGs.…”
Section: Introductionmentioning
confidence: 99%
“…In addition, the use of water (or aqueous biphasic mixtures) allows in many cases an easy catalyst/product separation, thus allowing the effective recycling of the catalytically active species, which is another key aspect in the Green Chemistry context [27]. However, despite the growing interest in aqueous catalysis, the use of this environmentally benign solvent in the hydrocarboxylation of alkynes been for long time neglected, probably due to the concerns of a competing hydration of the alkyne substrates to form carbonyl compounds, a process that is also catalyzed by transition metals [1][2][3][4][5][6]28]. In fact, in a general review on the "catalytic reactions of alkynes in water", published by Chen and Li in 2006, no examples of hydrocarboxylation reactions were collected [28].…”
Section: Introductionmentioning
confidence: 99%
“…However, despite the growing interest in aqueous catalysis, the use of this environmentally benign solvent in the hydrocarboxylation of alkynes been for long time neglected, probably due to the concerns of a competing hydration of the alkyne substrates to form carbonyl compounds, a process that is also catalyzed by transition metals [1][2][3][4][5][6]28]. In fact, in a general review on the "catalytic reactions of alkynes in water", published by Chen and Li in 2006, no examples of hydrocarboxylation reactions were collected [28]. Catalytic systems able to operate selectively in aqueous environments have only appeared in the literature in recent years, and are the subject of the present review article.…”
Section: Introductionmentioning
confidence: 99%