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Air-Stable Nickel Precatalysts for Fast and Quantitative Cross-Coupling of Aryl Sulfamates with Aryl Neopentylglycolboronates at Room Temperature

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journal contribution
posted on 19.12.2014, 00:00 by Ryan L. Jezorek, Na Zhang, Pawaret Leowanawat, Matthew H. Bunner, Nicholas Gutsche, Aleksander K. R. Pesti, James T. Olsen, Virgil Percec
A library containing 10 air-stable NiIIX­(Aryl)­(PCy3)2 σ-complexes as precatalysts (X = Cl, Br, OTs, OMs, aryl = 1-naphthyl, 2-naphthyl; X = Cl, 1-acenaphthenyl, 1-(2-methoxynaphthyl), 9-phenanthrenyl, 9-anthracyl) was synthesized and demonstrated to quantitatively cross-couple 2-methoxyphenyl dimethylsulfamate with methyl 4-(5,5-dimethyl-1,3,2-dioxaborinane-2-yl)­benzoate at 23 °C in dry THF in the presence of K3PO4(H2O)3.2 in less than 60 min. Lower or higher amounts of H2O in K3PO4 and as received THF mediate the same transformation in a maximum three times longer reaction time.