ArticleJournal of the American Chemical Society2023
Reductive Arylation of Nitroarenes with Chloroarenes: Reducing Conditions Enable New Reactivity from Palladium Catalysts.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Pd/NHC catalyzed reduction and coupling of nitroaromatics for the synthesis of diarylamines.RSC advances · 2024Article
- Dual role of nitroarenes as electrophiles and arylamine surrogates in Buchwald-Hartwig-type coupling for C-N bond construction.Chemical science · 2024Article
- Reductive coupling of nitro compounds with boronic acid derivatives: an overview.RSC advances · 2023Review
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Authors and funding
2 authors.
Funding
Abstract
Palladium-catalyzed C-N bond forming reactions are a key tool in modern synthetic organic chemistry. Despite advances in catalyst design enabling the use of a variety of aryl (pseudo)halides, the necessary aniline coupling partner is often synthesized in a discrete reduction step from a nitroarene. An ideal synthetic sequence would avoid the necessity of this step while maintaining the reliable reactivity of palladium catalysis. Herein, we describe how reducing conditions enable new chemical steps and reactivity from well-studied palladium catalysts, resulting in a new, useful transformation: the reductive arylation of nitroarenes with chloroarenes to form diarylamines. Mechanistic experiments suggest that under reducing conditions, BrettPhos-palladium complexes catalyze the dual
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