Journal
GREEN CHEMISTRY
Volume 20, Issue 15, Pages 3436-3443Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8gc01356j
Keywords
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Funding
- NSF [GOALI SusChEM 1566212, CNS-0960316]
- Novartis
- NIH [1S10OD012077]
- Center for Scientific Computing at the CNSI [DMR-1121053]
- Center for Scientific Computing at the MRL: NSF MRSEC [DMR-1121053]
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A new biaryl phosphine-containing platform can be constructed in only two steps. It complexes Pd(OAc)(2) forming a precursor of a very active catalyst useful for Suzuki-Miyaura cross-couplings of functionalized substrates. By a combination of pre-activation, used together with the uncommon solvent EtOAc, the resulting catalyst system is effective at loadings in the ppm (0.1-0.5 mol%) range with highly functionalized reaction partners. Similar reactions run in water containing nanomicelles are as fast or faster. The derived Pd-complexed pre-catalyst possesses extended bench stability. The resulting technology represents an attractive green synthetic advance in highly valued Suzuki-Miyaura couplings.
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