Journal
ORGANIC LETTERS
Volume 12, Issue 8, Pages 1784-1787Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol100410k
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Funding
- NIGMS NIH HHS [R01 GM068443-05, GM068443, R01 GM068443] Funding Source: Medline
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The BF3 center dot OEt2 center dot 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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