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Miyaura joined
Hokkaido University as a research associate in the A. Suzuki research group and as an associate professor. In 1994, Miyaura became a full professor at the university still working in the A. Suzuki group. In 2010, he retired from Hokkaido University but was allowed to honorarily retain his title as a specially appointed professor.
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In 1997, Miyaura created a new catalytic cycle starting from transmetalation which resulted in an aryl- or 1-alkenylrhodium(I) intermediate for 1,4-addition of aryl- or 1-alkenylboronic acids to α,β-unsaturated carbonyl compounds. This reaction turned out to have application in a variety of addition
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which is also known as the Suzuki-Miyaura cross-coupling reaction. In the cross-coupling reaction, the coupling partners are an organohalide and a boronic acid with a palladium(0) complex catalyst. This reaction is used to synthesize polyolefins, styrenes, and substituted biphenyls. In this reaction,
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Norio
Miyaura was born in Hokkaido, Japan in 1946. Miyaura received his bachelors in chemical engineering from Hokkaido University in 1969. He next received his masters in chemical engineering from Hokkaido University in 1971. Lastly, he received his doctorate in chemical engineering from Hokkaido
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In 1971, Miyaura joined
Hokkaido University's Faculty of Engineering as a synthetic chemical engineering assistant. Miyaura joined the J.K.Kochi group at Indiana University as a postdoctoral fellow in 1981. During this time he studied the epoxidation of alkenes catalyzed by metal-salen complexes.
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Miyaura's research interests included metal-catalyzed reactions of organoboron compounds (specifically applications to organic synthesis in catalyzed hydroboration), rhodium- or palladium-catalyzed conjugate addition reactions of arylboronic acids, palladium-catalyzed cross-coupling reactions of
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was a
Japanese organic chemist. He was a professor of graduate chemical engineering at Hokkaido University. His major accomplishments surrounded his work in cross-coupling reactions / conjugate addition reactions of organoboronic acids (for C-C bond-forming reactions) and addition / coupling
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Bi to enones. From this he found that the reaction produced a stereogenic center on carbon. He then focused on asymmetric syntheses using chiral rhodium or palladium catalysts. In 1998, Miyaura created a new chiral ligand of bidentate bisphosphoramidite (Me-BIPAM) through the addition of a
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reaction. In this reaction, a catalytic system converts carbon-halogen bonds or carbon-hydrogen bonds into carbon-boron bonds. This reaction can generate boronates from vinyl or aryl halides with the cross-coupling of bis(pinacolato)diboron in basic conditions with a catalyst such as
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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.
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Suzuki, Akira (1999). "Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998". Journal of
Organometallic Chemistry. 576 (1–2): 147–168. doi:10.1016/S0022-328X(98)01055-9.
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Miyaura, Norio; Suzuki, Akira (1979). "Palladium-Catalyzed Cross-Coupling
Reactions of Organoboron Compounds". Chemical Reviews. 95 (7): 2457–2483. CiteSeerX 10.1.1.735.7660. doi:10.1021/cr00039a007.(Review)
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Suzuki, Akira (1991). "Synthetic
Studies via the cross-coupling reaction of organoboron derivatives with organic halides". Pure Appl. Chem. 63 (3): 419–422. doi:10.1351/pac199163030419.
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In 2007, Miyaura was recognized as a recipient of the Japan
Chemical Society Award for his achievements in the field of organic chemistry and for his high international reputation.
366:"Discussion Addendum for: PALLADIUM(0)-CATALYZED REACTION OF 9-ALKYL-9-BORABICYCLO[3.3.1]NONANE WITH 1-BROMO-1-PHENYLTHIOETHENE: 4-(3-CYCLOHEXENYL)-2-PHENYLTHIO-1-BUTENE"
341:"Discussion Addendum for: PALLADIUM(0)-CATALYZED REACTION OF 9-ALKYL-9-BORABICYCLO[3.3.1]NONANE WITH 1-BROMO-1-PHENYLTHIOETHENE: 4-(3-CYCLOHEXENYL)-2-PHENYLTHIO-1-BUTENE"
266:"Discussion Addendum for: PALLADIUM(0)-CATALYZED REACTION OF 9-ALKYL-9-BORABICYCLO[3.3.1]NONANE WITH 1-BROMO-1-PHENYLTHIOETHENE: 4-(3-CYCLOHEXENYL)-2-PHENYLTHIO-1-BUTENE"
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and coupling reactions of organometallic and organo-nonmetallic compounds. In 1998, he discovered the mechanism for a rhodium(I)-catalyzed
Grignard-type addition of ArB(OH)
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with M. Nomura E. S.. Miyaura was a world-known and accomplished researcher by the time he retired and so, in 2007, he won the Japan Chemical Society Award.
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reactions of diborons and boranes (to synthesize organoboronic acids and esters through B-C bond-forming reactions). He is also the co-author of
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a carbon-carbon single bond is formed by coupling a halide (R-X) with an organoboron species (R-B) using a palladium catalyst and a base.
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rhodium(I)-binap catalyst into an enantioselective 1,4-addition of aryl- and 1-alkenylboronic acids to cyclic and acyclic enones.
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organoboronic acids, and addition and coupling reactions of diborons and pinacolborane for the synthesis of organoboronic esters.
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to aldehydes. Then in 2003, Miyaura found a reaction for the 1,4-addition of palladium-catalyzed ArB(OH)
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138:(dppf). The reaction results in borylated products that can be used as coupling partners for the
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Rhodium or palladium-catalyzed conjugate addition reactions of organoboron compounds
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won the Nobel Prize in 2010 for the Suzuki-Miyaura cross-coupling reaction (
478:"Metal-Catalyzed Bond-Forming Reactions of Organoboronic Acids"
418:"Metal-Catalyzed Bond-Forming Reactions of Organoboronic Acids"
241:"Metal-Catalyzed Bond-Forming Reactions of Organoboronic Acids"
201:"Metal-Catalyzed Bond-Forming Reactions of Organoboronic Acids"
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The Miyaura-Ishiyama borylation reaction is also known as the
229:(Topics in Current Chemistry, 219 ed.). Springer.
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227:Cross-Coupling Reactions: A Practical Guide
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125:Borylation reaction of aromatic compounds
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78:Suzuki–Miyaura cross-coupling reaction
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131:Miyaura borylation
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162:References
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