Journal
CHEMICAL SCIENCE
Volume 11, Issue 20, Pages 5205-5212Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc00968g
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Funding
- NSF [18-56406]
- Novartis
- National Science Foundation [CNS-1725797]
- California NanoSystems Institute
- Materials Research Science and Engineering Center (MRSEC
- NSF) at UC Santa Barbara [DMR 1720256]
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A new biaryl phosphine-containing ligand from an active palladium catalyst for ppm level Suzuki-Miyaura couplings, enabled by an aqueous micellar reaction medium. A wide array of functionalized substrates including aryl/heteroaryl bromides are amenable, as are, notably, chlorides. The catalytic system is both general and highly effective at low palladium loadings (1000-2500 ppm or 0.10-0.25 mol%). Density functional theory calculations suggest that greater steric congestion in N(2)Phos induces increased steric crowding around the Pd center, helping to destabilize the 2 : 1 ligand-Pd(0) complex more for N(2)Phos than for EvanPhos (and less bulky ligands), and thereby favoring formation of the 1 : 1 ligand-Pd-o complex that is more reactive in oxidative addition to aryl chlorides.
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