Lewis acid-promoted Friedel-Crafts alkylation reactions with alpha-ketophosphate electrophiles.

Lewis acid-promoted Friedel-Crafts alkylation reactions with alpha-ketophosphate electrophiles.
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DOI:
10.1021/ol100410k
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发表时间:
2010-04-16
期刊:
影响因子:
5.2
通讯作者:
Johnson, Jeffrey S.
Johnson, Jeffrey S.
中科院分区:
化学1区
文献类型:
--
作者:
Smith, Austin G.;Johnson, Jeffrey S.

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The BF3·OEt2-promoted nucleophilic substitution of α-aryl-α-ketophosphates to afford α,α-diaryl ketone products is described. Electron-rich α-ketophosphates perform best, with electron-neutral and electron-poor substrates also tolerated. The reaction is tolerant of a range of aromatic, heteroaromatic and non-aromatic nucleophiles, with yields ranging from 44-84%. Enantioenriched starting material yields racemic product, suggesting an SN1 pathway via an acylcarbenium ion.
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