Some regioselective cross-coupling reactions of halopyridines and halopyrimidines

Simkovsky, Nadja M.; Ermann, Monika; Roberts, Stanley M.; Parry, David M.; Baxter, Anthony D.

doi:10.1039/b205027g

Cited by 28 publications

(6 citation statements)

References 18 publications

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“…3, 146.8, 140.2, 132.9, 130.2, 128.2, 126.0, 124.1, 123.5. 2-(Pyridin-3-yl)pyrimidine (8i). 29 White solid (130 mg, 83% yield): 1 H NMR (300 MHz, CDCl 3 ) δ 9. 65 (s, 1H), 8.86−8.84 (m, 2H), 8.72−8.68 (m, 2H), 7.45−7.43 (m, 1H), 7.28−7.25 (m, 1H); 13 C NMR (75 MHz, CDCl 3 ) δ 162.9, 157.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of Heteroaryl Compounds through Cross-Coupling Reaction of Aryl Bromides or Benzyl Halides with Thienyl and Pyridyl Aluminum Reagents

Zhou

et al. 2013

J. Org. Chem.

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An efficient method for synthesis of useful biaryl building blocks containing 2-thienyl, 3-thienyl, 2-pyridyl, and 3-pyridyl moieties was provided through cross-coupling reactions of aryl bromides or benzyl halides with heteroaryl aluminum reagents in the presence of Pd(OAc)2 and (o-tolyl)3P. The coupling reaction also worked efficiently with heteroaryl bromides affording series of heterobiaryl compounds. The reaction of phenylbromide with in situ prepared 3-pyridyl aluminum was demonstrated to afford the product 8a in high yield. Additionally, the catalytic system was also suited well for the coupling reaction of benzyl halides with pyridyl aluminum reagents to afford series of pyridyl-arylmethane.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of Heteroaryl Compounds through Cross-Coupling Reaction of Aryl Bromides or Benzyl Halides with Thienyl and Pyridyl Aluminum Reagents

Zhou

et al. 2013

J. Org. Chem.

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“…These results represent a substantial improvement on sulfur-mediated couplings for this class of bipyridine. More generally, with the exception of parent 2,2′-bipyridine, 2 , the Grignard method gave improved yields of bipyridine versus our organolithium method or Qin’s sulfoxide method. , Yields with palladium-catalyzed couplings were superior in 7 of the 10 cases available for comparison. − In total, 16 novel bis-heteroaryls were synthesized, demonstrating the potential of ligand-coupling reactions as a complementary approach and enabling access to previously unexplored bis-heteroaryls. Thus, pyridylsulfonium salts represent a common building block for synthesis of a library of 2,2′-, 2,3′-, and 2,4′-pyridine-heteroaryl compounds.…”

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confidence: 87%

Synthesis of Bis-heteroaryls Using Grignard Reagents and Pyridylsulfonium Salts

2021

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Herein are reported ligand-coupling reactions of Grignard reagents with pyridylsulfonium salts. The method has wide functional group tolerance and enables the formation of bis-heterocycle linkages, including 2,4′-, 2,3′-, and 2,2′-bipyridines, as well as pyridines linked to pyrimidines, pyrazines, isoxazoles, and benzothiophenes. The methodology was successfully applied to the synthesis of the natural products caerulomycin A and E.

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“…Even though there are many examples of the preparation of 2-pyridylmetallic halides via the reaction of halopyridines, a limited number of studies have been reported on the preparation of 3-pyridylmetallic halides. 3-Pyridylmagnesium [ 31 , 32 , 33 ], 3-pyridylzinc [ 34 ], 3–pyridylindium [ 35 , 36 , 37 ] halides and Suzuki reagents [ 38 , 39 , 40 , 41 , 42 , 43 ] are the most widely used reagents for the preparation of pyridine-containing compounds. Lithiation of 3-halopyridine followed by transmetallation with appropriate metals (Mg, Zn, In) afforded the corresponding 3-pyridylmetallic halides.…”

Section: Introductionmentioning

confidence: 99%

Recent Advance in Heterocyclic Organozinc and Organomanganese Compounds; Direct Synthetic Routes and Application in Organic Synthesis

Kim

Rieke

2010

Molecules

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A practical synthetic route for the preparation of 2-pyridyl and 3-pyridyl derivatives has been accomplished by utilizing a simple coupling reaction of stable 2-pyridylzinc bromides and 3-pyridylzinc bromides. The organozincs used in this study were easily prepared via the direct insertion of active zinc into the corresponding bromopyridines. The subsequent coupling reactions with a variety of different electrophiles have afforded the corresponding coupling products. Using highly active manganese, a variety of Grignard-type organomanganese reagents have been obtained. The subsequent coupling reactions of the resulting organomanganese reagents with several electrophiles have also been accomplished under mild conditions.

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Some regioselective cross-coupling reactions of halopyridines and halopyrimidines

Cited by 28 publications

References 18 publications

Synthesis of Heteroaryl Compounds through Cross-Coupling Reaction of Aryl Bromides or Benzyl Halides with Thienyl and Pyridyl Aluminum Reagents

Synthesis of Heteroaryl Compounds through Cross-Coupling Reaction of Aryl Bromides or Benzyl Halides with Thienyl and Pyridyl Aluminum Reagents

Synthesis of Bis-heteroaryls Using Grignard Reagents and Pyridylsulfonium Salts

Recent Advance in Heterocyclic Organozinc and Organomanganese Compounds; Direct Synthetic Routes and Application in Organic Synthesis

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