General cross-coupling reactions with adaptive dynamic homogeneous catalysis

Ghosh, Indrajit and Shlapakov, Nikita and Karl, Tobias A. and Dueker, Jonas and Nikitin, Maksim and Burykina, Julia V. and Ananikov, Valentine P. and Koenig, Burkhard (2023) General cross-coupling reactions with adaptive dynamic homogeneous catalysis. NATURE, 619 (7968). pp. 87-93. ISSN 0028-0836, 1476-4687

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: ARYL
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 01 Mar 2024 07:14
Last Modified: 01 Mar 2024 07:14
URI: https://pred.uni-regensburg.de/id/eprint/59235

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