Dual Photoredox and Gold Catalysis: Intermolecular Multicomponent Oxyarylation of Alkenes

Abstract

Intermolecular three-component oxyarylation reactions of simple alkenes have been developed using a dual gold and photoredox catalytic system. Inexpensive organic dyes could be employed as the photocatalyst using aryldiazonium salts, while the combination of gold and iridium catalysts allowed for diaryliodonium compounds to be employed as the source of the arene coupling partner. In both cases, a-arylated ether products were generated under remarkably mild conditions using readily accessible visible light sources.

Photoredox Catalysis in Organic Chemistry

“…93,94 Experimental and computational mechanistic studies support the generation of cationic Au(III)–aryl species 52 , which can then engage the alkene to ultimately deliver the arylated products. 94,95 As illustrated in Scheme 20c, this strategy has been extended to arylative Meyer–Schuster rearrangements, 96 C(sp)–C(sp 2 ) couplings, 97 arylative hydrations of alkynes, 96b and the synthesis of aryl phosphonates.…”

Room Temperature CP Bond Formation Enabled by Merging Nickel Catalysis and Visible‐Light‐Induced Photoredox Catalysis

“…In 2011, Sanford and co-workers published a seminal contribution on the arylation of unactivated arenes by combining palladium catalysis and visible-light photoredox catalysis. [3a] Since that study, many other transition metals, such as copper, [4] gold, [5] and rhodium, [6] have been subsequently introduced to this emerging research area. However, very recently, a milestone was reached in the field of photoredox/nickel dual catalysis when two elegant examples of this catalytic process appeared simultaneously.…”

Photokatalyse mit sichtbarem Licht: Welche Bedeutung hat sie für die organische Synthese?

“…Die Meerwein-Arylierung ist ein klassischer Ansatz für die Bildung von C(sp 2 )-C(sp 3 )-Bindungen. [53] 2.2.2. [48,49] Neben Aryldiazoniumsalzen kçnnen andere Verbindungen als Vorstufen von Arylradikalen dienen, und insbesondere Diaryliodoniumsalze [50] 49 wurden in verschiedenen Arylierungsmethoden eingesetzt.…”