Journal of Organic Chemistry 2012-05-04

Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate.

Gary A Molander, Livia N Cavalcanti

Index: J. Org. Chem. 77(9) , 4402-13, (2012)

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Abstract

Organotrifluoroborates have emerged as an alternative to toxic and air- and moisture-sensitive organometallic species for the synthesis of functionalized aryl and heteroaryl compounds. It has been shown that the trifluoroborate moiety can be easily converted into a variety of different substituents in a late synthetic stage. In this paper, we disclose a mild, selective, and convenient method for the ipso-nitrosation of organotrifluoroborates using nitrosonium tetrafluoroborate (NOBF(4)). Aryl- and heteroaryltrifluoroborates were converted into the corresponding nitroso products in good to excellent yields. This method proved to be tolerant of a broad range of functional groups.