Ni(NIXANTPHOS)-Catalyzed Mono-Arylation of Toluenes with Aryl Chlorides and Bromides

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 (pK a ≈ 43) t...

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Bibliographic Details
Published in:Organic letters 2019-03, Vol.21 (6), p.1735-1739
Main Authors: Jiang, Hui, Sha, Sheng-Chun, Jeong, Soo A, Manor, Brian C, Walsh, Patrick J
Format: Article
Language:English
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Summary: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 (pK a ≈ 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00294