A Novel Deprotonative Functionalization of Aromatics with Phosphazene Base

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[A novel deprotonative functionalization of aromatics with phosphazene base].

A novel type of deprotonative functionalization of aromatics was accomplished with a phosphazene base (t-Bu-P4 base). For various nitrogen heteroaromatics and benzene derivatives, deprotonative 1,2-additions proceeded with the t-Bu-P4 base and ZnI(2) as an additive in the presence of carbonyl compounds. The t-Bu-P4 base has both extremely strong Brønsted basicity and less nucleophilicity due to...

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Phosphazene base-promoted functionalization of aryltrimethylsilanes.

The activation of Ar-Si bonds in aryltrimethylsilane was investigated using a catalytic amount of t-Bu-P4 base and selective functionalizations of aryltrimethylsilanes in the absence of strong electron withdrawing groups on the aromatic rings were accomplished.

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Deprotonative cadmation of functionalized aromatics.

This communication describes the deproto-metalation of a large range of aromatics including heterocycles using a newly developed lithium-cadmium base; the reaction proceeds at room temperature with an excellent chemoselectivity and efficiency, and proved to be regioselective in most cases.

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Metal-free deprotonative functionalization of heteroaromatics using organic superbase catalyst.

Metal-free deprotonative functionalization of heteroaromatic compounds was achieved using an organic superbase catalyst; an organosilicon additive such as trimethylsilylpropyne was employed for activating the catalytic cycle of 1,2-addition to carbonyl compounds.

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Phosphazene base-catalyzed condensation of trimethylsilylacetate with carbonyl compounds.

The t-Bu-P4 base was found to be an excellent catalyst for the condensation of trimethylsilylacetate or trimethylacetonitrile with carbonyl compounds to form functionalized alkenes and beta-enaminoesters were also synthesized by the condensation with formanilides.

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ژورنال

عنوان ژورنال: ChemInform

سال: 2005

ISSN: 0931-7597,1522-2667

DOI: 10.1002/chin.200501218