Ni-catalyzed cross-couplings of aryl, benzyl, and alkyl thiols with aryl and heteroaryl iodides were accomplished in the presence of an Ir-photoredox catalyst. Highly chemoselective C-S cross-coupling was achieved versus competitive C-O and C-N cross-couplings. This C-S cross-coupling method exhibits remarkable functional group tolerance, and the reactions can be carried out in the presence of molecular oxygen. Mechanistic investigations indicated that the reaction proceeded through transient Ni(I)-species and thiyl radicals. Distinct from nickel-catalyzed cross-coupling reactions involving carbon-centered radicals, control experiments and spectroscopic studies suggest that this C-S cross-coupling reaction does not involve a Ni(0)-species.
Ni-catalyzed cross-couplings of aryl, benzyl, and alkyl thiols with n class="Chemical">aryl and heteroaryl iodides were accomplished in the presence of an Ir-photoredox catalyst. Highly chemoselective C-S cross-coupling was achieved versus competitive C-O and C-N cross-couplings. This C-S cross-coupling method exhibits remarkable functional group tolerance, and the reactions can be carried out in the presence of molecular oxygen. Mechanistic investigations indicated that the reaction proceeded through transient Ni(I)-species and thiyl radicals. Distinct from nickel-catalyzed cross-coupling reactions involving carbon-centered radicals, control experiments and spectroscopic studies suggest that this C-S cross-coupling reaction does not involve a Ni(0)-species.
Authors: Russell T Smith; Xiaheng Zhang; Juan A Rincón; Javier Agejas; Carlos Mateos; Mario Barberis; Susana García-Cerrada; Oscar de Frutos; David W C MacMillan Journal: J Am Chem Soc Date: 2018-12-10 Impact factor: 15.419
Authors: Christopher B Kelly; Niki R Patel; David N Primer; Matthieu Jouffroy; John C Tellis; Gary A Molander Journal: Nat Protoc Date: 2017-02-02 Impact factor: 13.491
Authors: Ya Du; Ryan M Pearson; Chern-Hooi Lim; Steven M Sartor; Matthew D Ryan; Haishen Yang; Niels H Damrauer; Garret M Miyake Journal: Chemistry Date: 2017-08-01 Impact factor: 5.236