Brown hydroboration
E595505
Brown hydroboration is a landmark organic chemistry reaction developed by Herbert C. Brown that adds boron and hydrogen across carbon–carbon multiple bonds with high regio- and stereoselectivity.
All labels observed (2)
| Label | Occurrences |
|---|---|
| Brown hydroboration canonical | 1 |
| Hydroboration | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T6493422 — 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.
NED1
Entity disambiguation (via context triple)
gpt-5-mini-2025-08-07
Target entity: Brown hydroboration Context triple: [Herbert C. Brown, knownFor, Brown hydroboration]
-
A.
Barton reaction
The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
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B.
Barton–McCombie deoxygenation
Barton–McCombie deoxygenation is an organic chemistry reaction that converts alcohols into the corresponding hydrocarbons via radical-mediated removal of the hydroxyl group.
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C.
Corey–Bakshi–Shibata reduction
The Corey–Bakshi–Shibata reduction is a widely used asymmetric organic reaction that enantioselectively reduces ketones to chiral alcohols using a chiral oxazaborolidine catalyst and borane.
-
D.
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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E.
Buchwald–Hartwig amination
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.
- F. None of above. chosen
- G. Unsure - the case is ambiguous/there is not enough information to decide.
NED2
Entity disambiguation (via description)
gpt-5-mini-2025-08-07
Target entity: Brown hydroboration Target entity description: Brown hydroboration is a landmark organic chemistry reaction developed by Herbert C. Brown that adds boron and hydrogen across carbon–carbon multiple bonds with high regio- and stereoselectivity.
-
A.
Barton reaction
The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
-
B.
Barton–McCombie deoxygenation
Barton–McCombie deoxygenation is an organic chemistry reaction that converts alcohols into the corresponding hydrocarbons via radical-mediated removal of the hydroxyl group.
-
C.
Corey–Bakshi–Shibata reduction
The Corey–Bakshi–Shibata reduction is a widely used asymmetric organic reaction that enantioselectively reduces ketones to chiral alcohols using a chiral oxazaborolidine catalyst and borane.
-
D.
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.
-
E.
Buchwald–Hartwig amination
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.
- F. None of above. chosen
Statements (46)
| Predicate | Object |
|---|---|
| instanceOf |
addition reaction
ⓘ
hydroboration reaction ⓘ organic reaction ⓘ organoborane chemistry method ⓘ |
| addsAcrossBond |
carbon–carbon double bond
ⓘ
carbon–carbon triple bond ⓘ |
| addsAtom |
boron
ⓘ
hydrogen ⓘ |
| awardContext | contributed to Herbert C. Brown receiving the Nobel Prize in Chemistry ⓘ |
| bondFormation |
C–B bond
ⓘ
C–H bond ⓘ |
| developedBy | Herbert C. Brown ⓘ |
| field | organic chemistry ⓘ |
| followUpTransformation | oxidation to alcohol ⓘ |
| hasReactant |
alkene
ⓘ
alkyne ⓘ borane reagent ⓘ |
| intermediate | organoborane ⓘ |
| limitation | sensitive to air and moisture for some borane reagents ⓘ |
| mechanismType | concerted mechanism ⓘ |
| namedAfter | Herbert C. Brown ⓘ |
| oxidizingSystem | hydrogen peroxide in basic solution ⓘ |
| productFromAlkene | anti-Markovnikov alcohol ⓘ |
| productFromInternalAlkyne | ketone after oxidation ⓘ |
| productFromTerminalAlkyne | aldehyde after oxidation ⓘ |
| reactionType | electrophilic addition ⓘ |
| regioselectivity | anti-Markovnikov ⓘ |
| relatedChemistry | organoboron chemistry ⓘ |
| relatedReaction | hydroboration–oxidation ⓘ |
| safetyConsideration | borane reagents can be pyrophoric ⓘ |
| selectivityFeature |
high regioselectivity
ⓘ
high stereoselectivity ⓘ |
| solvent |
ether solvent
ⓘ
tetrahydrofuran ⓘ |
| stereochemicalOutcome | retention of relative configuration ⓘ |
| stereoselectivity | syn addition ⓘ |
| teachingContext | standard topic in undergraduate organic chemistry ⓘ |
| temperature | often room temperature ⓘ |
| typicalReagent |
9-borabicyclo[3.3.1]nonane
ⓘ
BH3·SMe2 ⓘ BH3·THF ⓘ catecholborane ⓘ disiamylborane ⓘ |
| uses |
synthesis of alcohols
ⓘ
synthesis of carbonyl compounds from alkynes ⓘ |
| yearOfKeyWork | 1950s ⓘ |
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.
Instruction
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.
Input
Subject: Brown hydroboration Description of subject: Brown hydroboration is a landmark organic chemistry reaction developed by Herbert C. Brown that adds boron and hydrogen across carbon–carbon multiple bonds with high regio- and stereoselectivity.
Referenced by (2)
Full triples — surface form annotated when it differs from this entity's canonical label.
subject linked to:
Herbert Brovarnik
linked to: Brown hydroboration