Buchwald-hartwig amination

- The Buchwald-Hartwig reaction in its original scope is an organic reaction describing a coupling reaction between an arylhalide and an amine in presence of base and a palladium catalyst forming a new carbon-nitrogen bond.   


- The reaction is conceptually related to the Stille reaction and the Heck reaction and its scope extends to oxygen nucleophiles like phenols and carbon nucleophiles like malonates. It replaced to an extent the copper catalysed Goldberg reaction.

Patents references

Step Conditions Patent
a Pd2dba3 / BINAP / Cs2CO3 / Toluene WO2010016005 (Pfizer)
Step Conditions Patent
a tert-Bu-Xphos / Pd2dba3 / NaOtBu / tert-butanol / dioxane   WO2010026110 (Roche)
Step Conditions Patent
a Pd(AcO)2 / BINAP / Cs2CO3 / dioxane WO2010010184 Galapagos
Step Conditions Patent
a Mopholine / Pd(AcO)2 / 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene / Cs2CO3 / dioxane WO2010049731 (Astrazeneca)
Step Conditions Patent
a Xantphos / Pd(AcO)2 / Cs2CO3 / THF WO2009158431 (Novartis)
Step Conditions Patent
a (9,9-dimethyl-9H-xanthene-4,5-diyl)-bis[diphenyl phosphine] / Pd(OAc)2 / Cs2CO3 / Toluene WO2010015972 (Pfizer)
Step Conditions Patent
a Pd(OAc)2 / BINAP / Cs2CO3 / dioxane   WO2010026122 (Novartis)

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