Palladium-Catalyzed para-C-H Arylation of Anilines with Aromatic Halides.
Anilines
Arylation
Biphenyls
Palladium
Para C−H Activation
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
21 Nov 2022
21 Nov 2022
Historique:
received:
08
07
2022
pubmed:
17
9
2022
medline:
17
9
2022
entrez:
16
9
2022
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 36112053
doi: 10.1002/anie.202210009
pmc: PMC9828783
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202210009Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : EXC-2033-390677874-Resolv and SFBTRR88 "3MET"
Organisme : Bundesministerium für Bildung und Forschung
Organisme : Human Resource Development Group
ID : CSIR-SRF
Organisme : Ministerium für Innovation, Wissenschaft und Forschung des Landes Nordrhein-Westfalen
Informations de copyright
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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