Direkt zum Inhalt

Ghosh, Indrajit ; Shlapakov, Nikita S. ; Karl, Tobias A. ; Düker, Jonas ; Nikitin, Maksim ; Burykina, Julia V. ; Ananikov, Valentine P. ; König, Burkhard

General cross-coupling reactions with adaptive dynamic homogeneous catalysis

Artikel

Ghosh, Indrajit , Shlapakov, Nikita S., Karl, Tobias A. , Düker, Jonas , Nikitin, Maksim , Burykina, Julia V., Ananikov, Valentine P. und König, Burkhard (2023) General cross-coupling reactions with adaptive dynamic homogeneous catalysis. Nature.

DOI zum Zitieren dieses Dokuments: 10.5283/epub.55044


Zusammenfassung

Cross-coupling reactions are among the most important transformations in modern organic synthesis(1-3). Although the range of reported (het)aryl halides and nucleophile coupling partners is very large considering various protocols, the reaction conditions vary considerably between compound classes, necessitating renewed case-by-case optimization of the reaction conditions(4). Here we introduce ...

Cross-coupling reactions are among the most important transformations in modern organic synthesis(1-3). Although the range of reported (het)aryl halides and nucleophile coupling partners is very large considering various protocols, the reaction conditions vary considerably between compound classes, necessitating renewed case-by-case optimization of the reaction conditions(4). Here we introduce adaptive dynamic homogeneous catalysis (AD-HoC) with nickel under visible-light-driven redox reaction conditions for general C(sp(2))-(hetero)atom coupling reactions. The self-adjustive nature of the catalytic system allowed the simple classification of dozens of various classes of nucleophiles in cross-coupling reactions. This is synthetically demonstrated in nine different bond-forming reactions (in this case, C(sp(2))-S, Se, N, P, B, O, C(sp(3), sp(2), sp), Si, Cl) with hundreds of synthetic examples under predictable reaction conditions. The catalytic reaction centre(s) and conditions differ from one another by the added nucleophile, or if required, a commercially available inexpensive amine base.



Beteiligte Einrichtungen


Details

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftNature
VerlagNATURE PORTFOLIO
Open Access ArtKein Open Access
Ort der VeröffentlichungBERLIN
Datum14 Juni 2023
Veröffentlichungsdatum20 Nov 2023 10:56
InstitutionenChemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Identifikationsnummer
WertTyp
10.1038/s41586-023-06087-4DOI
Stichwörter / KeywordsARYL
Dewey-Dezimal-Klassifikation500 Naturwissenschaften und Mathematik > 540 Chemie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenJa
URN der UB Regensburgurn:nbn:de:bvb:355-epub-550445
Dokumenten-ID55044

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