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Issue 19, 2010
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Undecahydro-closo-dodecaborates as good leaving groups in organic synthesis: generation of substituted styrenes via elimination of arylethyl dodecaborates

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Abstract

New functionalized arylethyl undecahydro-closo-dodecaborates (S,S-disubstituted B12H11SH2−, N,N-disubstituted B12H11NH3 and O-substituted B12H11OH2−) are prepared by a simple one-step reaction. Moderate to good yields are obtained in the presence of various functional aryl groups. The synthesis of functionalized styrene derivatives can be readily achieved by treating arylethyl undecahydro-closo-dodecaborates with various bases. The scope and limitations of this procedure are demonstrated by investigating an array of alkylated dodecaborates. Based on an E2 elimination reaction, we identify the mechanistic pathway for dealkylation of arylethyl dodecaborates. Mechanistic studies indicate the following essential requirements to promote the elimination reaction: (i) the presence of α-CH acidity of the phenethyl group; (ii) steric hindrance; (iii) a substituted heteroatom on the closo-B12H112− cage and (iv) the presence of an electron-withdrawing group on the aromatic ring.

Graphical abstract: Undecahydro-closo-dodecaborates as good leaving groups in organic synthesis: generation of substituted styrenes via elimination of arylethyl dodecaborates

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Publication details

The article was received on 12 Apr 2010, accepted on 29 Jun 2010 and first published on 13 Aug 2010


Article type: Paper
DOI: 10.1039/C005032F
Citation: Org. Biomol. Chem., 2010,8, 4427-4435
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    Undecahydro-closo-dodecaborates as good leaving groups in organic synthesis: generation of substituted styrenes via elimination of arylethyl dodecaborates

    A. R. Genady and H. Nakamura, Org. Biomol. Chem., 2010, 8, 4427
    DOI: 10.1039/C005032F

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