Artículo
Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C−S/C−N Couplings
Autor/es | Martín García, María Trinidad
Marín Gómez, Mario Maya Díaz, Celia María Prieto Cárdenas, María Auxiliadora Nicasio Jaramillo, María del Carmen |
Departamento | Universidad de Sevilla. Departamento de Química Inorgánica |
Fecha de publicación | 2021 |
Fecha de depósito | 2021-12-14 |
Publicado en |
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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. ... 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. |
Agencias financiadoras | Agencia Estatal de Investigación. España CTQ2017-82893- C2-2-R |
Identificador del proyecto | CTQ2017-82893- C2-2-R
US126226 |
Cita | Martín García, M.T., Marín Gómez, M., Maya Díaz, C.M., Prieto Cárdenas, M.A. y Nicasio Jaramillo, M.d.C. (2021). Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C−S/C−N Couplings. Chemistry - A European Journal, 27 (48), 12320-12326. |
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