Barton–McCombie deoxygenation
E395221
Barton–McCombie deoxygenation is an organic chemistry reaction that converts alcohols into the corresponding hydrocarbons via radical-mediated removal of the hydroxyl group.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Barton–McCombie deoxygenation canonical | 2 |
How this entity was disambiguated
This entity first appeared as the object of triple T3877956 — 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: Barton–McCombie deoxygenation Context triple: [Derek H. R. Barton, notableWork, Barton–McCombie deoxygenation]
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A.
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.
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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 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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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.
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.
- F. None of above. chosen
- G. Unsure - the case is ambiguous/there is not enough information to decide.
Target entity: Barton–McCombie deoxygenation Target entity description: Barton–McCombie deoxygenation is an organic chemistry reaction that converts alcohols into the corresponding hydrocarbons via radical-mediated removal of the hydroxyl group.
-
A.
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.
-
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 aminohydroxylation
Sharpless aminohydroxylation is a stereoselective chemical reaction that converts alkenes into vicinal amino alcohols using a chiral catalyst, widely used in asymmetric synthesis.
-
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.
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.
- F. None of above. chosen
Statements (49)
| Predicate | Object |
|---|---|
| instanceOf |
name reaction
ⓘ
organic reaction ⓘ radical reaction ⓘ |
| appliedIn |
complex molecule synthesis
ⓘ
late-stage functional group manipulation ⓘ natural product synthesis ⓘ |
| converts | alcohols ⓘ |
| development |
photoredox-catalyzed variants
ⓘ
tin-free variants ⓘ |
| field | organic chemistry ⓘ |
| initiationMethod |
photochemical initiation
ⓘ
thermal initiation ⓘ |
| keyIntermediate |
carbon-centered radical
ⓘ
thiocarbonyl derivative ⓘ xanthate ester ⓘ |
| keyStep | formation of thiocarbonyl derivative ⓘ |
| limitation | use of toxic organotin reagents ⓘ |
| mechanism | radical-mediated ⓘ |
| mechanisticStep |
generation of carbon radical from xanthate
ⓘ
homolytic cleavage of C–S bond ⓘ hydrogen atom abstraction by carbon radical ⓘ |
| namedAfter |
Derek H. R. Barton
ⓘ
Stuart W. McCombie ⓘ |
| originalPublicationJournal | Journal of the Chemical Society, Perkin Transactions 1 ⓘ |
| overallEffect | replacement of OH by hydrogen ⓘ |
| product | hydrocarbons ⓘ |
| publicationYear | 1975 ⓘ |
| reactionType | deoxygenation ⓘ |
| relatedReaction |
Barton decarboxylation
ⓘ
radical dehalogenation ⓘ |
| removes | oxygen atom from alcohol ⓘ |
| selectivity | chemoselective for C–O bond reduction ⓘ |
| stereochemicalOutcome | often leads to loss of stereochemistry at carbon center ⓘ |
| transformsFunctionalGroup | hydroxyl group ⓘ |
| typicalSolvent |
benzene
ⓘ
toluene ⓘ xylene ⓘ |
| typicalSubstrate |
primary alcohol
ⓘ
secondary alcohol ⓘ tertiary alcohol ⓘ |
| usesHydrogenAtomDonor |
Bu3SnH
ⓘ
organosilane reagent ⓘ tributyltin hydride ⓘ tris(trimethylsilyl)silane ⓘ |
| usesRadicalInitiator |
AIBN
ⓘ
azobisisobutyronitrile ⓘ |
| usesReagent |
thiocarbonate reagent
ⓘ
thiocarbonylimidazole reagent ⓘ xanthate reagent ⓘ |
How these facts were elicited
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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: Barton–McCombie deoxygenation Description of subject: Barton–McCombie deoxygenation is an organic chemistry reaction that converts alcohols into the corresponding hydrocarbons via radical-mediated removal of the hydroxyl group.
Referenced by (2)
Full triples — surface form annotated when it differs from this entity's canonical label.