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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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
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Language:English
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cited_by cdi_FETCH-LOGICAL-a415t-725673223ceeabd4c69a3415bebfaaf205f0dc4a173881a7c598e7eb21c4d3363
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container_end_page 1739
container_issue 6
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container_title Organic letters
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creator Jiang, Hui
Sha, Sheng-Chun
Jeong, Soo A
Manor, Brian C
Walsh, Patrick J
description 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.
doi_str_mv 10.1021/acs.orglett.9b00294
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title Ni(NIXANTPHOS)-Catalyzed Mono-Arylation of Toluenes with Aryl Chlorides and Bromides
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