Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 18, Pages 11799-11812Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01692
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Funding
- NSF CAREER [CHE-1848090]
- Montana State University
- NSF REU program [CHE-1461218, CHE-170089]
- NSF
- Murdock Charitable Trust Foundation [2015066, CoBRE NIGMS P20GM103546]
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Two N-heterocyclic carbene ligands provide orthogonal chemo-selectivity during the Pd-catalyzed Suzuki-Miyaura (SM) cross-coupling of chloroaryl triflates. The use of SIPr [SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene] leads to selective cross-coupling at chloride, while the use of SIMes [SIMes = 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene] provides selective coupling at triflate. With most chloroaryl triflates and arylboronic acids, ligand-controlled selectivity is high (>= 10:1). The scope of this methodology is significantly more general than previously reported methods for selective SM coupling of chloroaryl triflates using phosphine ligands. Density functional theory studies suggest that palladium's ligation state during oxidative addition is different with SIMes compared to SIPr.
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