:Miyaura borylation
{{Reactionbox
|Name = Miyaura borylation
|Type = Organic redox reaction
|NamedAfter = Norio Miyaura
|Section3 = {{Reactionbox Identifiers
|OrganicChemistryNamed = 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.{{cite journal |last1=Ishiyama|first1=Tatsuo|last2=Murata|first2=Miki|author3-link=Norio Miyaura |last3=Miyaura|first3=Norio|date=1 November 1995|title=Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic Esters|url= |journal=The Journal of Organic Chemistry|volume=60|issue=23|pages=7508–7510|doi=10.1021/jo00128a024}}
Scope
The Miyaura borylation has shown to work for:
Alkyl halides,{{cite journal |last1=Dudnik|first1=Alexander S.|last2=Fu|first2=Gregory C.|date=6 June 2012|title=Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon–Boron Bonds|url= |journal=J. Am. Chem. Soc.|volume=134 |issue=25|pages=10693–10697|doi=10.1021/ja304068t|pmid=22668072|pmc=3384763}} aryl halides,{{cite journal |last1=Rao|first1=Kanusu Umamaheswara|last2=Ventateswarlu|first2=Katta|date=16 March 2018|title=PdII-Porphyrin Complexes - the First Use as Safer and Efficient Catalysts for Miyaura Borylation|url= |journal=Synlett|volume=29|issue=8|pages=1055–1060|doi= 10.1055/s-0036-1591549|access-date=}}{{cite journal |last1=Tang|first1=Wenjun|last2=Keshipeddy|first2=Santosh|last3=Zhang|first3=Yongda|last4=Wei|first4=Xudong|last5=Savoie|first5=Jolaine|last6=Patel|first6=Nitinchandra D.|last7=Yee|first7=Nathan K.|last8=Senanayake|first8=Chris H.|date=18 March 2011|title=Efficient Monophosphorus Ligands for Palladium-Catalyzed Miyaura Borylation|url= |journal=Organic Letters|volume=13|issue=6|pages=1366–1369|doi=10.1021/ol2000556|pmid=21319836}} aryl halides using tetrahydroxydiboron,{{cite journal |last1=Molander|first1=Gary A.|last2=Trice|first2=Sarah L. J.|last3=Dreher|first3=Spencer D.|date=24 November 2010|title=Palladium-Catalyzed, Direct Boronic Acid Synthesis from Aryl Chlorides: A Simplified Route to Diverse Boronate Ester Derivatives|url= |journal=Journal of the American Chemical Society|volume=132|issue=50|pages=17701–17703|doi= 10.1021/ja1089759|pmid=21105666|pmc=3075417}} aryl halides using bis-boronic acid,{{cite journal |last1=Molander|first1=Gary A.|last2=Trice|first2=Sarah L. J.|last3=Kennedy|first3=Steven M.|date=20 September 2012|title=Scope of the Two-Step, One-Pot Palladium-Catalyzed Borylation/Suzuki Cross-Coupling Reaction Utilizing Bis-Boronic Acid|url= |journal=The Journal of Organic Chemistry|volume=77|issue=19|pages=8678–8688|doi=10.1021/jo301642v|pmid=22994557|pmc=3465529}} aryl triflates,{{cite journal |last1=Thompson|first1=Alicia L. S.|last2=Kabalka|first2=George W.|last3=Akula|first3=Murthy R.|last4=Huffman|first4=John W.|date=18 January 2005|title=The Conversion of Phenols to the Corresponding Aryl Halides Under Mild Conditions|url= |journal=Synthesis|volume= 2005|issue=4|pages=547–550|doi=10.1055/s-2005-861791}} aryl mesylates,{{cite journal |last1=Molander|first1=Gary A.|last2=Cavalcanti|first2=Livia N.|last3=García-García|first3=Caraolina|date=18 June 2013|title=Nickel-Catalyzed Borylation of Halides and Pseudohalides with Tetrahydroxydiboron [B2(OH)4]|url= |journal=The Journal of Organic Chemistry|volume=78|issue=13|pages=6427–6439|doi=10.1021/jo401104y|pmid=23777538|pmc=3740274}} vinyl halides,{{cite journal |last1=Takahashi|first1=Kou|last2=Takagi|first2=Jun|last3=Ishiyama|first3=Tatsuo|last4=Miyaura|first4=Norio|date=February 2000|title=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.|journal=Chemistry Letters|volume=29|issue=2|pages=126–127|doi=10.1246/cl.2000.126|hdl=2115/56184|access-date=|hdl-access=free}} vinyl halides of α,β-unsaturated carbonyl compounds,{{cite journal |last1=Takagi|first1=Jun|last2=Kamon|first2=Akahiro|last3=Ishiyama|first3=Tatsuo|last4=Miyaura|first4=Norio|date=November 2002|title=Synthesis of β-Boryl-α,β-unsaturated Carbonyl Compounds via Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with Vinyl Triflates|journal=Synlett|volume= 2002|issue=11|pages=1880–1882|doi=10.1055/s-2002-34869|hdl=2115/14605|hdl-access=free}} and vinyl triflates.{{cite journal |last1=Takagi|first1=Jun|last2=Takahashi|first2=Kou|last3=Ishiyama|first3=Tatsuo|last4=Miyaura|date=17 June 2002|title=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=Journal of the American Chemical Society|volume=124|issue=27|pages=8001–8006|doi=10.1021/ja0202255|pmid=12095344}}
See also
References
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