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

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 dimeth...

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Bibliographic Details
Published in:Organic letters 2014-12, Vol.16 (24), p.6326-6329
Main Authors: Jezorek, Ryan L., Zhang, Na, Leowanawat, Pawaret, Bunner, Matthew H., Gutsche, Nicholas, Pesti, Aleksander K. R., Olsen, James T., Percec, Virgil
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol503061c