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Synfacts 2008(3): 0298-0298  
DOI: 10.1055/s-2008-1042737
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

ortho Cupration via Direct Hydrogen-Copper Exchange

Contributor(s): Paul Knochel, Tobias Thaler
S. Usui, Y. Hashimoto, J. V. Morey, A. E. H. Wheatley*, M. Uchiyama*
RIKEN, Wako-shi and The University of Tokyo, Japan; University of Cambridge, UK
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Publication History

Publication Date:
21 February 2008 (online)

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Significance

A highly chemo- and regioselective protocol for the deprotonative cupration of functionalized arenes and heteroarenes with novel Lipshutz-type TMP-Cu-ate bases is reported. The special reactivity of the resulting aromatic copper compounds makes it a valuable complement to existing deprotonation methods which involve magnesium-, zinc-, or aluminum-based amides.