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September 27, 2025Open Access

De novo multicomponent assembly of diarylamines via photoredox/nickel dual catalysis

ZXZhehui XuShaanxi Normal University RMRui‐da MaShaanxi Normal University QLQi LiHarbin University of Science and Technology

Key Points

This method offers an efficient one-step synthesis of diarylamines, utilizing a novel three-component cascade approach.
The transformation was applied successfully to commercial drugs and natural products, proving its practical relevance in pharmaceuticals.
Preliminary mechanistic studies indicate the process likely follows a sequential pathway involving condensation, dehydrogenation, and cross-coupling.
This innovative strategy addresses limitations of traditional methods by allowing selective targeting of all positions on the aromatic ring.

Abstract

As essential structural motifs in pharmaceuticals and materials, diarylamines are reliably synthesized via transition-metal-catalyzed C–N coupling reactions between aryl electrophiles and pre-functionalized arylamines. Currently, the selective introduction of amino groups at specific positions (ortho-, meta-, or para-) on an aromatic ring to prepare arylamines are mainly achieved through transition-metal catalysis, requiring halogenated or borylated arenes as substrates. However, the installation of these directing groups onto aromatic units depends on the inherent reactivity patterns of the associated methods (e.g., electrophilic halogenation or C–H borylation), often making it impossible to selectively target all positions. This study overcomes this limitation through a de novo three-component cascade strategy, enabling the efficient one-step synthesis of diarylamines from cyclohexanone, aqueous ammonia, and haloarenes under photoredox/nickel dual catalysis. This method has been successfully applied to the synthesis of commercial drugs and has demonstrated its practical utility in the late-stage transformation of natural products and terpenes. Preliminary mechanistic studies suggest this transformation likely proceeds via a sequential condensation/dehydrogenation/cross-coupling pathway.

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