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]
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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]
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. 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. 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. 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.