Corey–Kim oxidation
E466667
Corey–Kim oxidation is an organic chemistry reaction that converts primary and secondary alcohols into aldehydes and ketones using N-chlorosuccinimide and dimethyl sulfide under mild conditions.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Corey–Kim oxidation canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T4741217 — 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: Corey–Kim oxidation Context triple: [E. J. Corey, developedMethod, Corey–Kim oxidation]
-
A.
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.
-
B.
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.
-
C.
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.
-
D.
Eschenmoser
Eschenmoser is a Swiss surname most notably associated with Albert Eschenmoser, a prominent organic chemist known for his pioneering work in the synthesis of complex natural products and studies on the origin of life.
-
E.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
- 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: Corey–Kim oxidation Target entity description: Corey–Kim oxidation is an organic chemistry reaction that converts primary and secondary alcohols into aldehydes and ketones using N-chlorosuccinimide and dimethyl sulfide under mild conditions.
-
A.
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.
-
B.
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.
-
C.
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.
-
D.
Eschenmoser
Eschenmoser is a Swiss surname most notably associated with Albert Eschenmoser, a prominent organic chemist known for his pioneering work in the synthesis of complex natural products and studies on the origin of life.
-
E.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
- F. None of above. chosen
Statements (45)
| Predicate | Object |
|---|---|
| instanceOf |
named reaction in organic chemistry
ⓘ
organic redox reaction ⓘ |
| advantage |
does not require heavy metals
ⓘ
operates under non-aqueous conditions ⓘ tolerates acid-sensitive functional groups ⓘ |
| avoidsOveroxidationTo | carboxylic acids ⓘ |
| byproduct |
dimethyl sulfide oxide (DMSO)
ⓘ
succinimide ⓘ |
| converts |
primary alcohols to aldehydes
ⓘ
secondary alcohols to ketones ⓘ |
| field | organic chemistry ⓘ |
| limitation | dimethyl sulfide has strong odor and toxicity concerns ⓘ |
| mechanismFeature |
activation of alcohol as alkoxysulfonium salt
ⓘ
beta-elimination to form carbonyl compound ⓘ formation of dimethylchlorosulfonium intermediate ⓘ |
| namedAfter |
Choung Un Kim
ⓘ
Elias James Corey ⓘ
linked to:
Elias J. Corey
|
| oxidantComponent | N-chlorosuccinimide ⓘ |
| product |
aldehydes
ⓘ
ketones ⓘ |
| publishedIn | Tetrahedron Letters ⓘ |
| reactionCondition |
mild conditions
ⓘ
typically low temperature ⓘ |
| reactionMedium | typically anhydrous conditions ⓘ |
| reactionType | oxidation of alcohols ⓘ |
| relatedTo |
PCC oxidation
ⓘ
Swern oxidation ⓘ |
| safetyConcern |
N-chlorosuccinimide is an oxidizing agent
ⓘ
requires handling of malodorous dimethyl sulfide ⓘ |
| selectivity |
chemoselective for alcohol oxidation
ⓘ
generally stops at aldehyde stage for primary alcohols ⓘ |
| stoichiometry |
uses stoichiometric N-chlorosuccinimide
ⓘ
uses stoichiometric dimethyl sulfide ⓘ |
| substrate |
primary alcohols
ⓘ
secondary alcohols ⓘ |
| sulfurComponent | dimethyl sulfide ⓘ |
| typicalPhase | homogeneous solution phase ⓘ |
| typicalTemperatureRange | −20 °C to room temperature ⓘ |
| usedFor |
laboratory-scale synthesis of aldehydes
ⓘ
laboratory-scale synthesis of ketones ⓘ |
| usedIn | total synthesis of natural products ⓘ |
| usesReagent |
N-chlorosuccinimide
ⓘ
dimethyl sulfide ⓘ |
| usesSolvent | dichloromethane ⓘ |
| yearOfPublication | 1972 ⓘ |
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: Corey–Kim oxidation Description of subject: Corey–Kim oxidation is an organic chemistry reaction that converts primary and secondary alcohols into aldehydes and ketones using N-chlorosuccinimide and dimethyl sulfide under mild conditions.
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.