Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate.

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.

DOI: 10.1021/jo300551m

Cite this paper

@article{Molander2012NitrosationOA, title={Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate.}, author={Gary A Molander and L{\'i}via Nunes Cavalcanti}, journal={The Journal of organic chemistry}, year={2012}, volume={77 9}, pages={4402-13} }