Miyaura borylation
| 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]
Scope[edit]
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[edit]
- Chan-Lam coupling
- Heck reaction
- Hiyama coupling
- Kumada coupling
- Negishi coupling
- Petasis reaction
- Sonogashira coupling
- Stille reaction
- Suzuki reaction
- List of organic reactions
References[edit]
- ^ a b 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.