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)
| Label | Occurrences |
|---|---|
| Suzuki coupling canonical | 2 |
| Suzuki–Miyaura coupling | 2 |
| Suzuki–Miyaura cross-coupling reaction | 2 |
| Stille coupling | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T3351790 — resolving that mention is where its identity was fixed. The disambiguator weighed these candidate entities and picked the highlighted one (or “None”, minting a new entity). This is how homonymy is resolved: the same surface form can point to different entities.
Target entity: Suzuki coupling Context triple: [Akira Suzuki, knownFor, Suzuki coupling]
-
A.
click chemistry
Click chemistry is a modular, high-yielding approach to chemical synthesis that uses simple, reliable reactions to rapidly assemble complex molecules, widely applied in drug discovery, materials science, and chemical biology.
-
B.
Sharpless epoxidation
Sharpless epoxidation is a landmark asymmetric oxidation reaction in organic chemistry that enables the enantioselective conversion of allylic alcohols to epoxides using chiral catalysts.
-
C.
Sharpless asymmetric dihydroxylation
Sharpless asymmetric dihydroxylation is a landmark chemical reaction that uses chiral catalysts to add two hydroxyl groups across an alkene with high enantioselectivity, revolutionizing asymmetric synthesis in organic chemistry.
-
D.
Fischer esterification
Fischer esterification is a classic acid-catalyzed organic reaction that forms esters from carboxylic acids and alcohols under reversible equilibrium conditions.
-
E.
Woodward–Hoffmann rules
The Woodward–Hoffmann rules are fundamental principles in organic chemistry that predict the stereochemistry and feasibility of pericyclic reactions based on orbital symmetry considerations.
- F. None of above. chosen
- G. Unsure - the case is ambiguous/there is not enough information to decide.
Target entity: Suzuki coupling Target entity description: 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.
-
A.
click chemistry
Click chemistry is a modular, high-yielding approach to chemical synthesis that uses simple, reliable reactions to rapidly assemble complex molecules, widely applied in drug discovery, materials science, and chemical biology.
-
B.
Sharpless epoxidation
Sharpless epoxidation is a landmark asymmetric oxidation reaction in organic chemistry that enables the enantioselective conversion of allylic alcohols to epoxides using chiral catalysts.
-
C.
Sharpless asymmetric dihydroxylation
Sharpless asymmetric dihydroxylation is a landmark chemical reaction that uses chiral catalysts to add two hydroxyl groups across an alkene with high enantioselectivity, revolutionizing asymmetric synthesis in organic chemistry.
-
D.
Fischer esterification
Fischer esterification is a classic acid-catalyzed organic reaction that forms esters from carboxylic acids and alcohols under reversible equilibrium conditions.
-
E.
Woodward–Hoffmann rules
The Woodward–Hoffmann rules are fundamental principles in organic chemistry that predict the stereochemistry and feasibility of pericyclic reactions based on orbital symmetry considerations.
- F. None of above. chosen
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
The pipeline generated the facts above by prompting gpt-5.1 with this entity's name + description and the instruction below.
You are a knowledge base construction expert. Given a subject entity and a description of it, return factual statements that you know for the subject as a JSON list of dictionaries(triples), where keys must be "subject", "predicate" and "object". The number of facts may be very high, between 25 to 50 or more, for very popular subjects. For less popular subjects, the number of facts can be very low, like 5 or 10. # Requirements - If you don't know the subject at all, return an empty list. - If the subject is not a named entity, return an empty list. - Include at least one triple where predicate is "instanceOf". - Do not get too wordy. - Separate several objects into multiple triples with one object.
Subject: Suzuki coupling Description of subject: 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.
Referenced by (7)
Full triples — surface form annotated when it differs from this entity's canonical label.