Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 7-8, Pages 1029-1034Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800768
Keywords
carbenes; Heck reaction; palladium; perimidinium salts; Suzuki coupling
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Funding
- DFG
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A novel lutidine-bridged bis-perimidinium dibromide 3 was synthesized in quantitative yield from cheap commercial starting materials. The bisylidene prepared therefrom in situ upon deprotonation is a potent precatalyst in palladium-catalyzed Heck and Suzuki cross-coupling reactions under aerobic conditions, and is efficient even with a ppm scale catalyst loading. Its stronger sigma-donor character is held to be responsible for its superior catalytic performance compared with imidazole- and benzimidazole-based analogues bearing the same skeleton precursors.
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