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.

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Label Occurrences
Buchwald–Hartwig amination canonical 1

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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

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Referenced by (1)

Full triples — surface form annotated when it differs from this entity's canonical label.

Stephen L. Buchwald knownFor Buchwald–Hartwig amination