title: Photoredox Mediated Nickel Catalyzed Cross-Coupling of Thiols With Aryl and Heteroaryl Iodides via Thiyl Radicals.
abstract: 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.
authors: Chemistry Department (Oncology), AstraZeneca Pharmaceuticals LP, Waltham, Massachusetts 02451, United States.
authors: Martins S
authors: MS
authors: Oderinde
authors: Département de Chimie, Université du Québec à Montréal , Montreal, Quebec, Canada , H2X 2J6.
authors: Mathieu
authors: M
authors: Frenette
authors: Chemistry Department (Oncology), AstraZeneca Pharmaceuticals LP, Waltham, Massachusetts 02451, United States.
authors: Daniel W
authors: DW
authors: Robbins
authors: Chemistry Department (Oncology), AstraZeneca Pharmaceuticals LP, Waltham, Massachusetts 02451, United States.
authors: Brian
authors: B
authors: Aquila
authors: Chemistry Department (Oncology), AstraZeneca Pharmaceuticals LP, Waltham, Massachusetts 02451, United States.
authors: Jeffrey W
authors: JW
authors: Johannes