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.
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 NERFINISHED ⓘ |
| 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 NERFINISHED ⓘ |
| 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 ⓘ |
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.