973-59-1

Upstream product

• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 100-46-9 benzylamine 

Downstream Products

• 165683-43-2 (E)-1-phenylpent-3-en-1-amine 
• 105251-34-1 (3S*,4S*)-4-amino-3-methyl-4-phenyl-1-butene 
• 105251-35-2 (3R*,4S*)-4-amino-3-methyl-4-phenyl-1-butene 
• 4383-23-7 1-phenyl-but-3-enylamine 
• 79232-19-2 (C₆H₅HCNC₆H₂(C₄H₉)2OH)2PdCl₂ 
• 79256-80-7 (C₆H₅HCNC₆H₂(C₄H₉)2OHPtCl₂(CH₂)2) 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Formal α-Allylation of Primary Amines by a Dearomative, Palladium-Catalyzed Umpolung Allylation of N-(Aryloxy)imines

N-(Aryloxy)imines, readily accessible by condensation/tautomerization of (pseudo)benzylic primary amines and 2,6-di-tert-butyl-1,4-benzoquinone, undergo efficient allylation to afford a wide range of homoallylic primary amines following hydrolytic workup. Deprotonation of N-(aryloxy)imines generates a delocalized 2-azaallyl anion-type nucleophile that engages in dearomative C-C bond-forming reactions with allylpalladium(II) electrophiles generated from allylic tert-butyl carbonates. This reactivity umpolung enables the formal α-allylation of (pseudo)benzylic primary amines. Mechanistic studies reveal that the apparent regioselectivity of the desired bond-forming event is a convergent process that is initiated by unselective allylation of N-(aryloxy)imines to give several regioisomeric species, which subsequently rearrange via stepwise [1,3]- or concerted [3,3]-sigmatropic shifts, ultimately converging to provide the desired regioisomer of the amine products.