Water-Promoted Organic Reactions

Lubineau, André; Augé, Jacques; Queneau, Yves

doi:10.1055/s-1994-25562

Cited by 455 publications

(161 citation statements)

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“…Recently, there has been increasing interest in the development of Barbier-Grignard-type reactions in water [6][7][8][9][10] . Many types of reactions that are traditionally conducted in organic solvents can be carried out in water with additional interesting features [9][10][11][12][13][14][15][16] , largely due to the inherent advantages of using aqueous organometallic reactions over those occurring in organic solvents [11][12][13][17][18][19] . For instance, there is the practical convenience of not having to handle inflammable and anhydrous organic solvents.…”

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confidence: 99%

The Barbier–Grignard-type arylation of aldehydes using unactivated aryl iodides in water

Zhou

2014

Nat Commun

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Carbon-carbon bond formation is the essence of organic synthesis. One of the most important methods for forming carbon-carbon bonds is the Barbier-Grignard-type reaction, which was discovered over a century ago. However, it is still highly desirable to further improve this process. In this article, we describe a Barbier-Grignard-type direct arylation of aldehydes by using unactivated iodides mediated by zinc and catalysed by rhodium in water. This method bypasses a number of challenges encountered by the conventional BarbierGrignard reaction, such as strict exclusion of moisture and air, protection-deprotection of various acidic hydrogens in the substrates, and so forth. It thereby creates a safer, more convenient and more environmentally benign strategy to access the diarylmethanols and aryl alkyl alcohols, ubiquitous skeletons found in fine chemicals, biologically active molecules and pharmaceuticals. Importantly, the same reaction performed in an organic solvent proceeded sluggishly to give much inferior yields.

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confidence: 99%

The Barbier–Grignard-type arylation of aldehydes using unactivated aryl iodides in water

Zhou

2014

Nat Commun

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“…The change of solvent can modify the activation energy, the solvation energy of reactants, and the transition state (40).…”

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confidence: 99%

Synthesis of highly substituted pyrroles using ultrasound in aqueous media

Almeida

2012

Green Chemistry Letters and Reviews

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A two-step protocol for the synthesis of highly substituted pyrroles in aqueous media and without catalyst is described. The first step is the dimerization of a 1,3-dicarbonyl compound by ceric ammonium nitrate/ultrasound to produce a tetracarbonyl derivative. This derivative is then combined with an amine in the absence of any catalysts to obtain the pyrrole via a PaalÁKnorr reaction. This route is an improvement when compared with classical methodologies toward Green Chemistry objectives.

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“…In the last decade, much attention has been paid to organometallic reactions in aqueous media [14]. Recently, transition metal selenolates or complexes have been widely used in synthesis of organoselenium compounds [15], but reports exploring zinc selenolates are rare [16].…”

Section: Resultsmentioning

confidence: 99%