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Synthesis of Fréchet-type Dendrimers with Tripodal Core via Staudinger/Aza-Wittig Reactions

Synthesis of Fréchet-type Dendrimers with Tripodal Core via Staudinger/Aza-Wittig Reactions

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Efficient stitching methods for the synthesis of tripodal Fréchet-type dendrimers containing secondary amineas a connector were elaborated. The synthetic strategy involved Staudinger/aza-Wittig reactions (new click reaction)between tripodal tris(azides) and aldehyde-dendrons in toluene in the presence of triphenylphosphine and followed by thereduction of imine intermediates. The tripodal core (1,3,5-tris-(3-azido-propoxy)-benzene) was chosen to serve as theazide functionalities for dendrimer growth. 1,3,5-Tris-(3-azido-propoxy)-benzene was stitched with the aldehyde-functionalizedFréchet-type dendrons via Staudinger/aza-Wittig reactions leading to the formation of the correspondingFréchet-type dendrimers in high yields.

Efficient stitching methods for the synthesis of tripodal Fréchet-type dendrimers containing secondary amineas a connector were elaborated. The synthetic strategy involved Staudinger/aza-Wittig reactions (new click reaction)between tripodal tris(azides) and aldehyde-dendrons in toluene in the presence of triphenylphosphine and followed by thereduction of imine intermediates. The tripodal core (1,3,5-tris-(3-azido-propoxy)-benzene) was chosen to serve as theazide functionalities for dendrimer growth. 1,3,5-Tris-(3-azido-propoxy)-benzene was stitched with the aldehyde-functionalizedFréchet-type dendrons via Staudinger/aza-Wittig reactions leading to the formation of the correspondingFréchet-type dendrimers in high yields.

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