Palladium‐Catalyzed para ‐C−H Arylation of Anilines with Aromatic Halides
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.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
Palladium‐Catalyzed para ‐C−H Arylation of Anilines with Aromatic Halides ; day:25 ; month:10 ; year:2022 ; extent:1
Angewandte Chemie / International edition. International edition ; (25.10.2022) (gesamt 1)
- Urheber
- DOI
-
10.1002/anie.202210009
- URN
-
urn:nbn:de:101:1-2022102615094887489534
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
15.08.2025, 07:26 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
Ähnliche Objekte (12)
Palladium-catalyzed \(\it para\)-C−H arylation of anilines with aromatic halides
Palladium-Catalyzed Benzylic Arylation
Palladium-Catalyzed Enantioselective Arylation of α-Imino Esters
Palladium-Catalyzed β-Arylation of α-Amino Esters
Palladium-catalyzed carbonylation reactions of aryl halides
Palladium-Catalyzed Oxidative Arylation of ortho-Phenylcarbamates with Arenes
Palladium-Catalyzed C (sp3)–H Arylation of Cyclic Peptides
Palladium-Catalyzed Direct Arylation of Chromium-Activated Benzylic C–H Groups
Synthesis of a Crushed Fullerene C60H24 through Sixfold Palladium‐Catalyzed Arylation
Palladium-Catalyzed Multiple S-Arylation for the Synthesis of Macrocyclic Peptides
The Heck Carbonylation: Palladium-Catalyzed Alkoxycarbonylation of Organic Halides
Palladium-Catalyzed C(sp3)–H Arylation of Peptides Assisted by Unmodified Asparagine
Palladium-catalyzed \(\it para\)-C−H arylation of anilines with aromatic halides
Palladium-Catalyzed Benzylic Arylation
Palladium-Catalyzed Enantioselective Arylation of α-Imino Esters
Palladium-Catalyzed β-Arylation of α-Amino Esters
Palladium-catalyzed carbonylation reactions of aryl halides
Palladium-Catalyzed Oxidative Arylation of ortho-Phenylcarbamates with Arenes
Palladium-Catalyzed C (sp3)–H Arylation of Cyclic Peptides
Palladium-Catalyzed Direct Arylation of Chromium-Activated Benzylic C–H Groups
Synthesis of a Crushed Fullerene C60H24 through Sixfold Palladium‐Catalyzed Arylation
Palladium-Catalyzed Multiple S-Arylation for the Synthesis of Macrocyclic Peptides
The Heck Carbonylation: Palladium-Catalyzed Alkoxycarbonylation of Organic Halides
Palladium-Catalyzed C(sp3)–H Arylation of Peptides Assisted by Unmodified Asparagine
Palladium-catalyzed \(\it para\)-C−H arylation of anilines with aromatic halides
Palladium-Catalyzed Benzylic Arylation
Palladium-Catalyzed Enantioselective Arylation of α-Imino Esters
Palladium-Catalyzed β-Arylation of α-Amino Esters
Palladium-catalyzed carbonylation reactions of aryl halides
Palladium-Catalyzed Oxidative Arylation of ortho-Phenylcarbamates with Arenes
Palladium-Catalyzed C (sp3)–H Arylation of Cyclic Peptides
Palladium-Catalyzed Direct Arylation of Chromium-Activated Benzylic C–H Groups
Synthesis of a Crushed Fullerene C60H24 through Sixfold Palladium‐Catalyzed Arylation
Palladium-Catalyzed Multiple S-Arylation for the Synthesis of Macrocyclic Peptides
The Heck Carbonylation: Palladium-Catalyzed Alkoxycarbonylation of Organic Halides