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.

All labels observed (1)

Label Occurrences
Buchwald–Hartwig amination canonical 1

How this entity was disambiguated

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 ⓘ
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 ⓘ
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–Miyaura coupling ⓘ
linked to: Suzuki 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 ⓘ

How these facts were elicited

Referenced by (1)

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

Stephen L. Buchwald → knownFor → Buchwald–Hartwig amination ⓘ