Synthesis of functionalized 2-arylpyridines from 2-halopyridines and various aryl halides via a nickel catalysis

Gosmini, Corinne; Bassene‐Ernst, Carine; Durandetti, Muriel

doi:10.1016/j.tet.2009.05.044

Cited by 61 publications

(35 citation statements)

References 40 publications

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“…Moderate to excellent yields were obtained when the halopyridine was employed in moderate excess (1.3 equiv). A wide range of functional groups was tolerated such as amines, esters, nitriles and ketones 43…”

Section: Nickel Catalysismentioning

confidence: 99%

Reductive Cross‐Coupling Reactions between Two Electrophiles

Knappke¹,

Grupe²,

Gärtner³

et al. 2014

Chemistry A European J

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213

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Reductive cross-electrophile coupling reactions have recently been developed to a versatile and sustainable synthetic tool for selective C-C bond formation. The employment of cheap and abundant electrophiles avoids the pre-formation and handling of organometallic reagents. In situ reductive coupling is effected in the presence of a transition-metal catalyst (Ni, Co, Pd, Fe) and a suitable metallic reductant (Mn, Zn, Mg). This Concept article assesses the current state of the art and summarizes recent protocols with various combinations of alkyl, alkenyl, allyl, and aryl reagents and highlights key mechanistic studies.

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Section: Nickel Catalysismentioning

confidence: 99%

Reductive Cross‐Coupling Reactions between Two Electrophiles

Knappke¹,

Grupe²,

Gärtner³

et al. 2014

Chemistry A European J

Self Cite

600

213

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“…The difference in reactivity can be resulted when the aryl electrophiles display notable differences in electron density and bear different leaving groups. Likewise, the same group has shown that the coupling of 6-halopyridine with a variety of aryl halides can be effectively carried out under Nicatalyzed reaction conditions (Scheme 33, left) [89]. The initial use of 2-bromopyridine is highly competent for para-and meta-methoxycarbonyl phenyl bromides.…”

Section: Formation Of Biaryl Compoundsmentioning

confidence: 99%

Nickel-Catalyzed Reductive Couplings

2016

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The Ni-catalyzed reductive coupling of alkyl/aryl with other electrophiles has evolved to be an important protocol for the construction of C-C bonds. This chapter first emphasizes the recent progress on the Ni-catalyzed alkylation, arylation/vinylation, and acylation of alkyl electrophiles. A brief overview of CO2 fixation is also addressed. The chemoselectivity between the electrophiles and the reactivity of the alkyl substrates will be detailed on the basis of different Ni-catalyzed conditions and mechanistic perspective. The asymmetric formation of C(sp(3))-C(sp(2)) bonds arising from activated alkyl halides is next depicted followed by allylic carbonylation. Finally, the coupling of aryl halides with other C(sp(2))-electrophiles is detailed at the end of this chapter.

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“…The reaction demonstrates good chemoselectivity, with no coupling observed at the 2-position of 2-bromo- or 2-chloro-5-iodopyridine (see products 7 a and 7 b ). 13 Whereas substitution meta to the iodide was tolerated (7 f ), a decrease in yield was observed when the substituent was ortho to the iodide (7 g ). Iodo-pyridines or -pyrimidines lacking substitution at C2 were poor substrates, presumably due to the increased Lewis basicity of the nitrogen.…”

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confidence: 99%

Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles

2015

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A Ni-catalyzed asymmetric reductive cross-coupling of heteroaryl iodides and α-chloronitriles has been developed. This method furnishes enantioenriched α,α-disubstituted nitriles from simple organohalide building blocks. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, quinolines, thiophenes, and piperidines. The reaction proceeds under mild conditions at room temperature, and precludes the need to pre-generate organometallic nucleophiles.

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Synthesis of functionalized 2-arylpyridines from 2-halopyridines and various aryl halides via a nickel catalysis

Cited by 61 publications

References 40 publications

Reductive Cross‐Coupling Reactions between Two Electrophiles

Reductive Cross‐Coupling Reactions between Two Electrophiles

Nickel-Catalyzed Reductive Couplings

Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles

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