Literature DB >> 20235527

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

Austin G Smith1, Jeffrey S Johnson.   

Abstract

The BF(3).OEt(2)-promoted nucleophilic substitution of alpha-aryl-alpha-ketophosphates to afford alpha,alpha-diaryl ketone products is described. Electron-rich alpha-ketophosphates perform best, with electron-neutral and electron-poor substrates also tolerated. The reaction is tolerant of a range of aromatic, heteroaromatic, and nonaromatic nucleophiles, with yields ranging from 44% to 84%. Enantioenriched starting material yields racemic product, suggesting an S(N)1 pathway via an acylcarbenium ion.

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Year:  2010        PMID： 20235527      PMCID： PMC2852482          DOI： 10.1021/ol100410k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

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