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J Am Chem Soc. 2014 Nov 19;136(46):16439-43. doi: 10.1021/ja509548z. Epub 2014 Nov 6.

Silver-catalyzed radical fluorination of alkylboronates in aqueous solution.

Author information

1
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, Peoples's Republic of China.

Abstract

We report herein an efficient and general method for the deboronofluorination of alkylboronates. Thus, with the catalysis of AgNO3, the reactions of various alkylboronic acids or their pinacol esters with Selectfluor reagent in acidic aqueous solution afforded the corresponding alkyl fluorides under mild conditions. A broad substrate scope and wide functional group compatibility were observed. A radical mechanism is proposed for this site-specific fluorination.

PMID:
25350556
DOI:
10.1021/ja509548z
[Indexed for MEDLINE]

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