Palladium-catalysed reactions of aryl halides with soft, non-organometallic nucleophiles

Prim, Damien; Campagne, Jean‐Marc; Joseph, Delphine; Andrioletti, Bruno

doi:10.1016/s0040-4020(02)00076-5

Cited by 370 publications

(115 citation statements)

References 267 publications

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“…The organic extracts were combined, washed with aqueous saturated NaHCO 3 (3 x 100 mL), water (3 x 100 mL), brine (2 x 50 mL), dried over anhydrous MgSO 4 , filtered and concentrated giving a colorless oil (2.64 g, 90%). 1 4 mmol), sulfuric acid (26 mL )and water (35 mL) was refluxed for 4 h. The reaction mixture was poured over ice and, after cooling to room temperature, extracted with ether (3 x 70 mL). The organic extracts were combined and evaporated giving a yellow solid.…”

Section: General Methodsmentioning

confidence: 99%

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Synthesis and characterization in solution and in the solid State of the palladium aryl bromide complexes [Pd(Ar)Br{(S)-BINAP}]: formation of cyclopalladated complexes and direct observation of a C-N reductive elimination to form heterocycles

Monteiro¹,

Davis²

2004

J. Braz. Chem. Soc.

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Section: General Methodsmentioning

confidence: 99%

“…1,2 In particular, Buchwald reported that aryl bromides with pendant secondary amide groups could be cyclized to form tertiary amides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization in solution and in the solid State of the palladium aryl bromide complexes [Pd(Ar)Br{(S)-BINAP}]: formation of cyclopalladated complexes and direct observation of a C-N reductive elimination to form heterocycles

Monteiro¹,

Davis²

2004

J. Braz. Chem. Soc.

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“…The Hirao reaction has now become an important P-C bond forming method since its discovery about 35 years ago. On further development and modifications, this method constitutes the current state of the art in the synthesis of P-C(sp2) bonds as documented in a number of reviews [13][14][15]. The Hirao reaction has been gradually extended to more aryl and vinyl derivatives and to variety of [P(O)H species, thus making available phosphonic, phosphinic and phosphine oxide derivatives as well [5].…”

Section: The Hirao Reactionmentioning

confidence: 99%

Microwave-assisted Hirao reaction: recent developments

Brahmachari

2015

ChemTexts

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Organic molecules containing phosphorus, now, constitute a major branch of chemistry, and offer fascinating possibilities for their structural, synthetic, and mechanistic study as well as promising biological activities. Organophosphorus compounds find numerous potential applications in the areas of industrial, agricultural, and medicinal chemistry. Aryl-and vinyl-phosphonates are an important class of organophosphorus compounds with potential biological relevance. The Hirao reaction offers a way to access these compounds through phosphorus-carbon (P-C) cross-coupling of aryl and vinyl halides with O,O-dialkyl phosphites, and this reaction has attained a commendable development in many ways in regard to the diversity in the substrates, [P(O)H species, catalysts, and reaction conditions. The present article deals with such developments that occurred under the influence of microwave irradiation.

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“…Despite palladium catalyzed methods to achieve diaryl ether structural scaffold, Hartwig et al reported the synthesis of biaryl ethers using sodium phenoxide and electron-deficient aryl bromides in the presence of ligand (dppf) [14]. Buchwald and co workers reported the C-O coupling reaction between aryl halides and phenols by using palladium as a catalyst [15][16][17][18][19]. In recent past palladium based complexes, [20][21][22] were explored for the synthesis of biaryl ethers.…”

Section: Introductionmentioning

confidence: 99%