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Updated: Jan 28, 2026

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Published on: June 23, 2019
Ni(NIXANTPHOS)-Catalyzed Mono-Arylation of Toluenes with Aryl Chlorides and Bromides
Hui Jiang1, Sheng-Chun Sha1, Soo A Jeong1
1Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.
Abstract:
A nickel-catalyzed cross-coupling of toluene derivatives with both aryl bromides and chlorides using a NIXANTPHOS-ligated nickel(II) complex has been developed. The key factor to success is proposed to be the catalyst activation of toluene by a cation-π complex, enabling methyl arenes (p Ka ≈ 43) to be deprotonated with the relatively mild base NaN(SiMe3)2. This method facilitates access to a variety of sterically and electronically diverse hetero- and nonheteroaryl-containing diarylmethanes.
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