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Título: | Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C−S/C−N Couplings |
Autor: | Martín, M. Trinidad; Marín, Mario; Maya, Celia CSIC ORCID; Prieto, María Auxiliadora CSIC ORCID ; Nicasio, M. Carmen | Palabras clave: | C−S bond formation Dual chemoselectivity Ni catalysis Phosphine complexes Tandem cross-couplings |
Fecha de publicación: | 2021 | Editor: | Wiley-VCH | Citación: | Chemistry - a European Journal, 27 (48): 12320-12326 (2021) | Resumen: | Ni-catalyzed C−S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C−O electrophiles in this context is almost uncharted. Here, we describe that preformed Ni(II) precatalysts of the type NiCl(allyl)(PMe2Ar’) (Ar’=terphenyl group) efficiently couple a wide range of (hetero)aryl halides, including challenging aryl chlorides, with a variety of aromatic and aliphatic thiols. Aryl and alkenyl tosylates are also well tolerated, demonstrating, for the first time, to be competent electrophilic partners in Ni-catalyzed C−S bond formation. The chemoselective functionalization of the C−I bond in the presence of a C−Cl bond allows for designing site-selective tandem C−S/C−N couplings. The formation of the two C-heteroatom bonds takes place in a single operation and represents a rare example of dual electrophile/nucleophile chemoselective process. | Versión del editor: | https://doi.org/10.1002/chem.202101906 | URI: | http://hdl.handle.net/10261/249398 | DOI: | 10.1002/chem.202101906 |
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