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Synfacts 2009(6): 0663-0663  
DOI: 10.1055/s-0029-1216694
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Imidazolylsulfonates: Stable and Highly Activated Electrophiles in Cross-Couplings

Contributor(s): Paul Knochel, Tobias Thaler
J. Albaneze-Walker*, R. Raju, J. A. Vance, A. J. Goodman, M. R. Reeder, J. Liao, M. T. Maust, P. A. Irish, P. Espino, D. R. Andrews
Schering-Plough Corporation, Union, USA
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Publikationsdatum:
25. Mai 2009 (online)

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Significance

Imidazolylsulfonates have been disclosed as superior alternatives to the unstable triflates and the unreactive tosylates in cross-coupling reactions, They can easily be synthesized from the corresponding phenols using 1,1′-sulfonyldiimidazole along with a substoichiometric amount of Cs2CO3 as base and were shown to also effectively undergo palladium-catalyzed hydrogenolysis and carbonylation reactions.