Direct synthesis of hetero-biaryl compounds containing an unprotected NH2 group via Suzuki–Miyaura reaction

Itoh, Takahiro; Mase, Toshiaki

doi:10.1016/j.tetlet.2005.03.053

Cited by 116 publications

(94 citation statements)

References 28 publications

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“…One equivalent of K 2 CO 3 led to the incomplete consumption of the starting material, whereas 3 or 4 equivalents of K 2 CO 3 led to an increase in the rate of hydrodehalogenation (entries [15][16][17]. Comparison of different solvent systems (entries [18][19][20] revealed a mixture of dioxane and water to be optimal for the reaction. We envisioned that a lower reaction temperature could potentially suppress the undesired hydrodehalogenation, however, the impurity 4 was formed even at 40°C.…”

Section: Resultsmentioning

confidence: 99%

4‐Arylation of N‐Acylamino‐ and Aminopyrazoles by the Suzuki–Miyaura Cross‐Coupling Reaction

Jedinák

Cankař

2016

Eur J Org Chem

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Halogenated aminopyrazoles have rarely been utilized in metal-catalysed cross-coupling reactions mainly due to the complexation of the aminopyrazoles to the metal center, which deactivates the catalyst. In this paper we reveal that the appropriate combination of palladium source and ligand enables efficient Suzuki-Miyaura cross-coupling reactions with even challenging substrates such as halogenated aminopyrazoles. The combination of Pd(OAc) 2 and XPhos allowed effi-

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Section: Resultsmentioning

confidence: 99%

4‐Arylation of N‐Acylamino‐ and Aminopyrazoles by the Suzuki–Miyaura Cross‐Coupling Reaction

Jedinák

Cankař

2016

Eur J Org Chem

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“…of phenylboronic acid at the reflux temperature of dioxane, the corresponding 4,6-diphenylpyrimidine 3b was obtained in 62% yield (entry 9). Compounds 1c,d [12,13] bearing strong electron-donating and capable to form complexes with palladium species amino group [14] in the position 2 of the pyrimidine ring reacted with phenylboronic acid only at elevated temperatures. Moreover, possibly due to decreased reactivity of chlorine groups, the cross-coupling reaction with 1.08 equiv.…”

Section: Resultsmentioning

confidence: 99%

Palladium‐catalyzed cross‐coupling reaction of 2‐ and/or 5‐substituted 4,6‐dichloropyrimidines with arylboronic acids

Tumkevičius

Dodonova

Baskirova

et al. 2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).The Suzuki-Miyaura reaction of some 4,6-dichloropyrimidines bearing methylthio-, methyl-, amino-, cyano-, formyl-, and nitro groups in positions 2 and/or 5 of the pyrimidine ring with arylboronic acids has been investigated. Influence of palladium catalyst, ligand, base, and solvent on the reaction outcome was studied. The reaction was found to give the corresponding 4,6-diarylpyrimidines in reasonable yields using Pd(OAc) 2 /PPh 3 /K 3 PO 4 or Pd(PPh 3 ) 2 Cl 2 /K 3 PO 4 as catalyst systems.

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“…In some cases primary or secondary amino groups have been masked by protective groups to allow the coupling of such substrates, while without N-protection the Suzuki coupling was less efficient. [39] Lacking general and efficient cross-coupling protocols, synthetic chemists resort to heteroaryl bromides as coupling substrates [40,41] instead of the cheaper and more easily available aryl chlorides, which require at least 1 mol % of catalyst for quantitative conversion. [42][43][44] Recently, significant improvements in the coupling of heteroaryl chlorides have been reported by Guram et al, [45,46] Buchwald et al [35] and Fu et al [33] Interestingly, some of the more efficient coupling reactions involving heterocyclic substrates were performed in water [25,[47][48][49][50][51][52][53][54][55][56][57][58][59][60] or in water-containing solvent mixtures (with toluene, dioxane, CH 3 …”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Suzuki–Miyaura Coupling of Heterocyclic Substrates through Rational Reaction Design

Fleckenstein

Plenio

2008

Chemistry A European J

121

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A dicyclohexyl(2-sulfo-9-(3-(4-sulfophenyl)propyl)-9H-fluoren-9-yl)phosphonium salt was synthesized in 64% overall yield in three steps from simple commercially available starting materials. The highly water-soluble catalyst obtained from the corresponding phosphine and [Na(2)PdCl(4)] enabled the Suzuki coupling of a broad variety of N- and S-heterocyclic substrates. Chloropyridines (-quinolines) and aryl chlorides were coupled with aryl-, pyridine- or indoleboronic acids in quantitative yields in water/n-butanol solvent mixtures in the presence of 0.005-0.05 mol % of Pd catalyst at 100 degrees C, chloropurines were quantitatively Suzuki coupled in the presence of 0.5 mol % of catalyst, and S-heterocyclic aryl chlorides and aryl- or 3-pyridylboronic acids required 0.01-0.05 mol % Pd catalyst for full conversion. The key to the high activity of the Pd-phosphine catalyst is the rational design of the reaction parameters (i.e., the presence of water in the reaction mixture, good solubility of reactants and catalyst in n-butanol/water (3:1), and the electron-rich and sterically demanding nature of the phosphine ligand).

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Direct synthesis of hetero-biaryl compounds containing an unprotected NH2 group via Suzuki–Miyaura reaction

Cited by 116 publications

References 28 publications

4‐Arylation of N‐Acylamino‐ and Aminopyrazoles by the Suzuki–Miyaura Cross‐Coupling Reaction

4‐Arylation of N‐Acylamino‐ and Aminopyrazoles by the Suzuki–Miyaura Cross‐Coupling Reaction

Palladium‐catalyzed cross‐coupling reaction of 2‐ and/or 5‐substituted 4,6‐dichloropyrimidines with arylboronic acids

Highly Efficient Suzuki–Miyaura Coupling of Heterocyclic Substrates through Rational Reaction Design

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