Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 12, Pages 1910-1915Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600075
Keywords
2-azaallyl anion; diarylmethylamines; NIXANTPHOS; regioselectivity; umpolung
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Funding
- Scientific and Technical Research Council of Turkey [TUBITAK-2219]
- CONACyT (Mexico)
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An umpolung synthesis of diarylmethylamine derivatives is presented. This reaction entails a palladium-catalyzed arylation of 1,3-diaryl-2-azaallyl anions, in situ generated from N-benzyl aldimines. A Pd(NIXANTPHOS)-based catalyst together with hindered silylamide bases enabled the coupling of aldimines with aryl bromides in good to excellent yields without product isomerization. Moreover, regioselectivity in the arylation of unsymmetrical 1,3-diaryl-2-azaallyl anions was studied. This method is suitable for a gram scale synthesis of diarylmethylamine derivatives at room temperature without use of a glove box.
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