Miyaura borylation

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Miyaura borylation
Named after Norio Miyaura
Reaction type Organic redox reaction
Identifiers
Organic Chemistry Portal miyaura-borylation-reaction

Miyaura borylation, also known as the Miyaura borylation reaction, is a named reaction in organic chemistry that allows for the generation of boronates from vinyl or aryl halides with the cross-coupling of bis(pinacolato)diboron in basic conditions with a catalyst such as PdCl2(dppf). The resulting borylated products can be used as coupling partners for the Suzuki reaction. [1]

Contents

Scope

The Miyaura borylation has shown to work for:

Alkyl halides, [2] aryl halides, [1] [3] [4] aryl halides using tetrahydroxydiboron, [5] aryl halides using bis-boronic acid, [6] aryl triflates, [7] aryl mesylates, [8] vinyl halides, [9] vinyl halides of α,β-unsaturated carbonyl compounds, [10] and vinyl triflates. [11]

See also

References

  1. 1 2 Ishiyama, Tatsuo; Murata, Miki; Miyaura, Norio (1 November 1995). "Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic Esters". The Journal of Organic Chemistry. 60 (23): 7508–7510. doi:10.1021/jo00128a024.
  2. ↑ Dudnik, Alexander S.; Fu, Gregory C. (6 June 2012). "Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon–Boron Bonds". J. Am. Chem. Soc. 134 (25): 10693–10697. doi:10.1021/ja304068t. PMC   3384763 . PMID   22668072.
  3. ↑ Rao, Kanusu Umamaheswara; Ventateswarlu, Katta (16 March 2018). "PdII-Porphyrin Complexes - the First Use as Safer and Efficient Catalysts for Miyaura Borylation". Synlett. 29 (8): 1055–1060. doi: 10.1055/s-0036-1591549 .
  4. ↑ Tang, Wenjun; Keshipeddy, Santosh; Zhang, Yongda; Wei, Xudong; Savoie, Jolaine; Patel, Nitinchandra D.; Yee, Nathan K.; Senanayake, Chris H. (18 March 2011). "Efficient Monophosphorus Ligands for Palladium-Catalyzed Miyaura Borylation". Organic Letters. 13 (6): 1366–1369. doi:10.1021/ol2000556. PMID   21319836.
  5. ↑ Molander, Gary A.; Trice, Sarah L. J.; Dreher, Spencer D. (24 November 2010). "Palladium-Catalyzed, Direct Boronic Acid Synthesis from Aryl Chlorides: A Simplified Route to Diverse Boronate Ester Derivatives". Journal of the American Chemical Society. 132 (50): 17701–17703. doi:10.1021/ja1089759. PMC   3075417 . PMID   21105666.
  6. ↑ Molander, Gary A.; Trice, Sarah L. J.; Kennedy, Steven M. (20 September 2012). "Scope of the Two-Step, One-Pot Palladium-Catalyzed Borylation/Suzuki Cross-Coupling Reaction Utilizing Bis-Boronic Acid". The Journal of Organic Chemistry. 77 (19): 8678–8688. doi:10.1021/jo301642v. PMC   3465529 . PMID   22994557.
  7. ↑ Thompson, Alicia L. S.; Kabalka, George W.; Akula, Murthy R.; Huffman, John W. (18 January 2005). "The Conversion of Phenols to the Corresponding Aryl Halides Under Mild Conditions". Synthesis. 2005 (4): 547–550. doi:10.1055/s-2005-861791.
  8. ↑ Molander, Gary A.; Cavalcanti, Livia N.; García-García, Caraolina (18 June 2013). "Nickel-Catalyzed Borylation of Halides and Pseudohalides with Tetrahydroxydiboron [B2(OH)4]". The Journal of Organic Chemistry. 78 (13): 6427–6439. doi:10.1021/jo401104y. PMC   3740274 . PMID   23777538.
  9. ↑ Takahashi, Kou; Takagi, Jun; Ishiyama, Tatsuo; Miyaura, Norio (February 2000). "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. 29 (2): 126–127. doi:10.1246/cl.2000.126. hdl: 2115/56184 .
  10. ↑ Takagi, Jun; Kamon, Akahiro; Ishiyama, Tatsuo; Miyaura, Norio (November 2002). "Synthesis of β-Boryl-α,β-unsaturated Carbonyl Compounds via Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with Vinyl Triflates". Synlett. 2002 (11): 1880–1882. doi:10.1055/s-2002-34869. hdl: 2115/14605 .
  11. ↑ Takagi, Jun; Takahashi, Kou; Ishiyama, Tatsuo; Miyaura (17 June 2002). "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. 124 (27): 8001–8006. doi:10.1021/ja0202255. PMID   12095344.
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