Display options
Cite
Jezorek RL, Zhang N, Leowanawat P, et al. Air-stable nickel precatalysts for fast and quantitative cross-coupling of aryl sulfamates with aryl neopentylglycolboronates at room temperature. Org Lett. 2014;16(24):6326-9doi: 10.1021/ol503061c.
Jezorek, R. L., Zhang, N., Leowanawat, P., Bunner, M. H., Gutsche, N., Pesti, A. K., Olsen, J. T., & Percec, V. (2014). Air-stable nickel precatalysts for fast and quantitative cross-coupling of aryl sulfamates with aryl neopentylglycolboronates at room temperature. Organic letters, 16(24), 6326-9. https://doi.org/10.1021/ol503061c
Jezorek, Ryan L, et al. "Air-stable nickel precatalysts for fast and quantitative cross-coupling of aryl sulfamates with aryl neopentylglycolboronates at room temperature." Organic letters vol. 16,24 (2014): 6326-9. doi: https://doi.org/10.1021/ol503061c
Jezorek RL, Zhang N, Leowanawat P, Bunner MH, Gutsche N, Pesti AK, Olsen JT, Percec V. Air-stable nickel precatalysts for fast and quantitative cross-coupling of aryl sulfamates with aryl neopentylglycolboronates at room temperature. Org Lett. 2014 Dec 19;16(24):6326-9. doi: 10.1021/ol503061c. Epub 2014 Dec 03. PMID: 25467653.
Copy Download .nbib Format: NLM
Share it on

Org Lett. 2014 Dec 19;16(24):6326-9. doi: 10.1021/ol503061c. Epub 2014 Dec 03.

Air-stable nickel precatalysts for fast and quantitative cross-coupling of aryl sulfamates with aryl neopentylglycolboronates at room temperature.

Organic letters

Ryan L Jezorek, Na Zhang, Pawaret Leowanawat, Matthew H Bunner, Nicholas Gutsche, Aleksander K R Pesti, James T Olsen, Virgil Percec

Affiliations

  1. Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.

PMID: 25467653 DOI: 10.1021/ol503061c

Abstract

A library containing 10 air-stable Ni(II)X(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.

Publication Types