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http://hdl.handle.net/10397/95494
Title: | General chemoselective suzuki-miyaura coupling of polyhalogenated aryl triflates enabled by an alkyl-heteroaryl-based phosphine ligand | Authors: | So, CM Yuen, OY Ng, SS Chen, Z |
Issue Date: | 2-Jul-2021 | Source: | ACS catalysis, 2 July 2021, v. 11, no. 13, p. 7820-7827 | Abstract: | This study describes a general chemoselective Suzuki-Miyaura coupling of polyhalogenated aryl triflates with the reactivity order of C-Cl > C-OTf using a Pd/L33 catalyst. The methine hydrogen and the steric hindrance offered by the alkyl bottom ring of L33 were found to be key factors in reactivity and chemoselectivity. With the Pd/ L33 catalyst, a wide range of polyhalogenated (hetero)aryl triflates, which were independent of the substrates and of the relative positioning of the competing reaction sites, coupled well with (hetero)aryl, alkenyl, and alkylboronic acids to obtain the corresponding products with good chemoselectivity and yields. The chemoselective reaction could easily be scaled up to the gram scale, and the use of parts per million levels of Pd catalyst (as low as 10 ppm Pd) was achieved. | Keywords: | Chemoselectivity Palladium Phosphine Polyhalogenated aryl triflates Suzuki−Miyaura coupling |
Publisher: | American Chemical Society | Journal: | ACS catalysis | EISSN: | 2155-5435 | DOI: | 10.1021/acscatal.1c02146 | Rights: | © 2021 American Chemical Society This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.1c02146. |
Appears in Collections: | Journal/Magazine Article |
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So_General_Chemoselective_Suzuki-Miyaura.pdf | Pre-Published version | 901.8 kB | Adobe PDF | View/Open |
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