Buchwald–Hartwig amination
E381391
The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Buchwald–Hartwig amination canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T3713934 — 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: Buchwald–Hartwig amination Context triple: [Stephen L. Buchwald, knownFor, Buchwald–Hartwig amination]
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A.
Suzuki coupling
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.
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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.
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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.
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D.
Sharpless aminohydroxylation
Sharpless aminohydroxylation is a stereoselective chemical reaction that converts alkenes into vicinal amino alcohols using a chiral catalyst, widely used in asymmetric synthesis.
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E.
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.
- F. None of above. chosen
- G. Unsure - the case is ambiguous/there is not enough information to decide.
Target entity: Buchwald–Hartwig amination Target entity description: The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
-
A.
Suzuki coupling
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.
-
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.
Sharpless aminohydroxylation
Sharpless aminohydroxylation is a stereoselective chemical reaction that converts alkenes into vicinal amino alcohols using a chiral catalyst, widely used in asymmetric synthesis.
-
E.
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.
- F. None of above. chosen
Statements (62)
| Predicate | Object |
|---|---|
| instanceOf |
carbon–nitrogen bond-forming reaction
ⓘ
cross-coupling reaction ⓘ named reaction in organic chemistry ⓘ palladium-catalyzed reaction ⓘ |
| advantage |
broad substrate scope
ⓘ
high functional group tolerance ⓘ mild reaction conditions ⓘ |
| application |
agrochemical synthesis
ⓘ
fine chemical synthesis ⓘ material science ⓘ pharmaceutical synthesis ⓘ |
| baseExamples |
cesium carbonate
ⓘ
potassium tert-butoxide ⓘ sodium tert-butoxide ⓘ |
| baseRequired | strong base ⓘ |
| catalyst |
palladium
ⓘ
palladium(0) complex ⓘ palladium(II) complex ⓘ |
| developedBy |
John F. Hartwig
NERFINISHED
ⓘ
Stephen L. Buchwald ⓘ |
| developedIn | 1990s ⓘ |
| field |
catalysis
ⓘ
organic chemistry ⓘ organometallic chemistry ⓘ |
| formsBond | C–N bond ⓘ |
| ligandType |
biaryl phosphine ligand
ⓘ
bidentate phosphine ligand ⓘ phosphine ligand ⓘ |
| mechanisticStep |
amine coordination
ⓘ
deprotonation ⓘ oxidative addition ⓘ reductive elimination ⓘ |
| metalCenter |
palladium(0) intermediate
ⓘ
palladium(II) intermediate ⓘ |
| namedAfter |
John F. Hartwig
NERFINISHED
ⓘ
Stephen L. Buchwald ⓘ |
| nucleophile |
alkyl amine
ⓘ
amine ⓘ aniline ⓘ primary amine ⓘ secondary amine ⓘ |
| product |
N-arylated amine
ⓘ
aryl amine ⓘ diaryl amine ⓘ |
| reactionType | cross-coupling of aryl halides with amines ⓘ |
| relatedTo |
Chan–Lam coupling
ⓘ
Suzuki coupling ⓘ
surface form:
Suzuki–Miyaura coupling
Ullmann reaction ⓘ |
| selectivity | chemoselective C–N coupling ⓘ |
| substrate |
aryl bromide
ⓘ
aryl chloride ⓘ aryl halide ⓘ aryl iodide ⓘ vinyl halide ⓘ |
| typicalSolvent |
dimethylformamide
ⓘ
dioxane ⓘ toluene ⓘ |
| typicalTemperature | elevated temperature ⓘ |
| usedFor |
late-stage functionalization of drug candidates
ⓘ
synthesis of diarylamines ⓘ synthesis of heteroaryl amines ⓘ synthesis of triarylamines ⓘ |
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: Buchwald–Hartwig amination Description of subject: The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.