Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 33, Pages 9502-+Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201503941
Keywords
alkyl zinc reagents; cross-coupling; N-heterocyclic carbenes; palladium; transition-metal catalysis
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Funding
- NSERC Canada
- Eli Lilly Research Award Program (LRAP)
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The ability to cross-couple secondary alkyl centers is fraught with a number of problems, including difficult reductive elimination, which often leads to -hydride elimination. Whereas catalysts have been reported that provide decent selectivity for the expected (non-rearranged) cross-coupled product with aryl or heteroaryl oxidative-addition partners, none have shown reliable selectivity with five-membered-ring heterocycles. In this report, a new, rationally designed catalyst, Pd-PEPPSI-IHept(Cl), is demonstrated to be effective in selective cross-coupling reactions with secondary alkyl reagents across an impressive variety of furans, thiophenes, and benzo-fused derivatives (e.g., indoles, benzofurans), in most instances producing clean products with minimal, if any, migratory insertion for the first time.
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