Suzuki coupling

E351603

Suzuki coupling is a widely used palladium-catalyzed cross-coupling reaction that forms carbon–carbon bonds between organoboron compounds and organic halides, fundamental in organic synthesis and pharmaceutical chemistry.

All labels observed (4)

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Statements (57)

Predicate Object
instanceOf carbon–carbon bond-forming reaction
cross-coupling reaction
organic reaction
palladium-catalyzed reaction
advantage compatibility with aqueous media
mild reaction conditions
tolerance of many functional groups
use of relatively nontoxic organoboron reagents
applicationArea materials science
natural product synthesis
organic synthesis
pharmaceutical chemistry
catalyst palladium
developedBy Akira Suzuki NERFINISHED
Norio Miyaura NERFINISHED
firstReportedIn 1979
formsBondBetween aryl and aryl groups
aryl and vinyl groups
sp2 carbon centers
vinyl and vinyl groups
formsBondType C–C bond
hasAlternativeName Suzuki coupling
surface form: Suzuki–Miyaura coupling
mechanisticStep oxidative addition
reductive elimination
transmetalation
namedAfter Akira Suzuki NERFINISHED
Norio Miyaura NERFINISHED
NobelLaureateAssociated Akira Suzuki NERFINISHED
recognizedBy Nobel Prize in Chemistry 2010
relatedReaction Heck reaction
Kumada coupling
Negishi coupling
Sonogashira coupling
Suzuki coupling self-linksurface differs
surface form: Stille coupling
requires base
typicalBase carbonate base
hydroxide base
organic amine base
phosphate base
typicalCatalyst Pd(0) complex
Pd(II) complex
typicalSolvent mixture of water and organic solvent
polar aprotic solvent
usesReagent alkenyl halide
alkenylboronic acid
alkyl halide
alkylboronic acid
aryl halide
arylboronic acid
organic halide
organoboron compound
organoboronic acid
organoboronic ester
pseudohalide
triflate
vinyl halide
vinylboronic acid

How these facts were elicited

Referenced by (7)

Full triples — surface form annotated when it differs from this entity's canonical label.

Akira Suzuki knownFor Suzuki coupling
Akira Suzuki knownFor Suzuki coupling
this entity surface form: Suzuki–Miyaura cross-coupling reaction
Akira Suzuki coDeveloperOf Suzuki coupling
Akira Suzuki coDeveloperOf Suzuki coupling
this entity surface form: Suzuki–Miyaura cross-coupling reaction
Suzuki coupling hasAlternativeName Suzuki coupling
this entity surface form: Suzuki–Miyaura coupling
Suzuki coupling relatedReaction Suzuki coupling self-linksurface differs
this entity surface form: Stille coupling
Buchwald–Hartwig amination relatedTo Suzuki coupling
this entity surface form: Suzuki–Miyaura coupling