ArticleAngewandte Chemie (International ed. in English)2022
Palladium-Catalyzed para-C-H Arylation of Anilines with Aromatic Halides.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
What it found
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Who cites it
7 citing papers in PubMed, 22 citations in OpenAlex.
- Regioselective Synthesis of Benzylsilanols from Kobayashi-Type Reagents via C(spAngewandte Chemie (International ed. in English) · 2026Article
- Illuminating Synergistic Catalysis: SET-HAT Unlocks Proximal C-H Arylation of Aromatic Amines.JACS Au · 2026Article
- Understanding the Regiodivergence between Hydroarylation and Trifluoromethylarylation of 1,3-Dienes Using Anilines in HFIP.JACS Au · 2024Article
- Trifluoromethylarylation of alkenes using anilines.Chemical science · 2023Article
- On Prototropy and Bond Length Alternation in Neutral and Ionized Pyrimidine Bases and Their Model Azines in Vacuo.Molecules (Basel, Switzerland) · 2023Review
- Palladium-CatalyzedACS catalysis · 2022Article
- Palladium-Catalyzed para-C-H Arylation of Anilines with Aromatic Halides.Angewandte Chemie (International ed. in English) · 2022Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
Abstract
Controlling regioselectivity in C-H functionalizations is a key challenge in chemical method development. In arenes, functionalizations are most difficult to direct towards the C-H group furthest away from a substituent, in its para position. We herein demonstrate how the para-C-H arylation of anilines with non-activated aryl halides, elusive to date, is achieved by a base-assisted "metalla-tautomerism" approach. A proton is abstracted from the aniline substrate and replaced by an arylpalladium species, generated from the aryl halide coupling partner. In this step, the palladium is directed away from the N- to the tautomeric para-C-H position by a large phosphine ligand combined with a triphenylmethyl shielding group. The triphenylmethyl group is easily installed and removed, and can be recycled.
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Registered trials
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