Journal
RSC ADVANCES
Volume 5, Issue 24, Pages 18960-18971Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ra00505a
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Funding
- U.S. Department of Energy [DESC0002142]
- NSF (ERC) [EEC-0813570]
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Aqueous Sonogashira coupling between lipophilic terminal alkynes and aryl bromides or iodides gave moderate to high yields at 40 degrees C using readily available and inexpensive surfactants (2.0 w/v% in water) such as SDS and CTAB. The catalyst precursor was 2 mol% Pd(PPh3)(2)Cl-2, and included a 5 mol% Cu(I) co-catalyst for aryl iodide substrates. Aryl-bromide reagents were found to be inhibited by iodide and Cu(I). Studies under Cu(I)-free conditions reveal two competing pathways. A deprotonation pathway gives rise to the traditional Sonogashira product (3), while a carbopalladation pathway produces enyne, 5. The surfactant solution (SDS or CTAB) can be recycled up to three times for coupling between 1-octyne and 1-iodonapthalene in the presence of CuI before the yields decrease.
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