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Mijaurova borylace

chemická reakce

Mijaurova borylace, také nazývaná Mijaurova borylační reakce, je organická reakce, při které se tvoří boronáty z vinyl- nebo arylhalogenidů párováním s bis(pinakoláto)diborem v zásaditém prostředí za katalýzy PdCl2(dppf). Vzniklé borylované sloučeniny lze zapojit do Suzukiových reakcí.[1]

Rozsah editovat

Při Mijaurově borylaci lze jako substráty použít alkylhalogenidy,[2] samotné arylhalogenidy,[1][3][4] arylhalogenidy s tetrahydroxydiborem,[5] arylhalogenidy s bis-boronovými kyselinami,[6] aryltrifláty,[7] arylmesyláty,[8] vinylhalogenidy,[9] vinylhalogenidy α,β-nenasycených karbonylových sloučenin[10] a vinyltrifláty.[11]

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Související články editovat

Reference editovat

V tomto článku byl použit překlad textu z článku Miyaura borylation na anglické Wikipedii.

  1. ↑ a b Tatsuo Ishiyama; Miki Murata; Norio Miyaura. Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic Esters. The Journal of Organic Chemistry. 1995-11-01, s. 7508–7510. DOI 10.1021/jo00128a024. 
  2. ↑ Alexander S. Dudnik; Gregory C. Fu. Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon–Boron Bonds. Journal of the American Chemical Society. 2012-06-06, s. 10693–10697. DOI 10.1021/ja304068t. PMID 22668072. 
  3. ↑ Kanusu Umamaheswara Rao; Katta Ventateswarlu. PdII-Porphyrin Complexes - the First Use as Safer and Efficient Catalysts for Miyaura Borylation. Synlett. 2018-03-16, s. 1055–1060. DOI 10.1055/s-0036-1591549. 
  4. ↑ Wenjun Tang; Santosh Keshipeddy; Yongda Zhang; Xudong Wei; Jolaine Savoie; Nitinchandra D. Patel; Nathan K. Yee. Efficient Monophosphorus Ligands for Palladium-Catalyzed Miyaura Borylation. Organic Letters. 2011-03-18, s. 1366–1369. DOI 10.1021/ol2000556. PMID 21319836. 
  5. ↑ Gary A. Molander; Sarah L. J. Trice; Spencer D. Dreher. Palladium-Catalyzed, Direct Boronic Acid Synthesis from Aryl Chlorides: A Simplified Route to Diverse Boronate Ester Derivatives. Journal of the American Chemical Society. 2010-11-24, s. 17701–17703. DOI 10.1021/ja1089759. PMID 21105666. 
  6. ↑ Gary A. Molander; Sarah L. J. Trice; Steven M. Kennedy. Scope of the Two-Step, One-Pot Palladium-Catalyzed Borylation/Suzuki Cross-Coupling Reaction Utilizing Bis-Boronic Acid. The Journal of Organic Chemistry. 2012-09-20, s. 8678–8688. DOI 10.1021/jo301642v. PMID 22994557. 
  7. ↑ Alicia L. S. Thompson; George W. Kabalka; Murthy R. Akula; John W. Huffman. The Conversion of Phenols to the Corresponding Aryl Halides Under Mild Conditions. Synthesis. 2005-01-18, s. 547–550. DOI 10.1055/s-2005-861791. 
  8. ↑ Gary A. Molander; Livia N. Cavalcanti; Caraolina García-García. Nickel-Catalyzed Borylation of Halides and Pseudohalides with Tetrahydroxydiboron [B2(OH)4]. The Journal of Organic Chemistry. 2013-06-18, s. 6427–6439. DOI 10.1021/jo401104y. PMID 23777538. 
  9. ↑ Kou Takahashi; Jun Takagi; Tatsuo Ishiyama; Norio Miyaura. 1-Alkenylboronic acid pinacol esters can be synthesized via a palladium-catalyzed cross-coupling reaction of 1-alkenyl halides or triflates with bis(pinacolato)diboron in toluene at 50°C in the presence of potassium phenoxide and PdCl2(PPh3)2·2PPh3.. Chemistry Letters. 2000, s. 126–127. DOI 10.1246/cl.2000.126. 
  10. ↑ Jun Takagi; Akahiro Kamon; Tatsuo Ishiyama; Norio Miyaura. Synthesis of β-Boryl-α,β-unsaturated Carbonyl Compounds via Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with Vinyl Triflates. Synlett. 2002, s. 1880–1882. DOI 10.1055/s-2002-34869. 
  11. ↑ Jun Takagi; Kou Takahashi; Tatsuo Ishiyama; Norio Miyaura. Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with 1-Alkenyl Halides or Triflates: Convenient Synthesis of Unsymmetrical 1,3-Dienes via the Borylation-Coupling Sequence. Journal of the American Chemical Society. 2002-06-17, s. 8001–8006. DOI 10.1021/ja0202255. PMID 12095344. 
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