General cross-coupling reactions with adaptive dynamic homogeneous catalysis
Ghosh, Indrajit
, Shlapakov, Nikita S., Karl, Tobias A.
, Düker, Jonas
, Nikitin, Maksim
, Burykina, Julia V., Ananikov, Valentine P.
and König, Burkhard
(2023)
General cross-coupling reactions with adaptive dynamic homogeneous catalysis.
Nature 619, pp. 87-93.
Date of publication of this fulltext: 22 Jun 2023 08:09
Article
DOI to cite this document: 10.5283/epub.54398
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 ...
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.
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| Item type | Article | ||||
| Journal or Publication Title | Nature | ||||
| Publisher: | NATURE PORTFOLIO | ||||
|---|---|---|---|---|---|
| Place of Publication: | BERLIN | ||||
| Volume: | 619 | ||||
| Page Range: | pp. 87-93 | ||||
| Date | 14 June 2023 | ||||
| Institutions | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König | ||||
| Identification Number |
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| Keywords | ARYL | ||||
| Dewey Decimal Classification | 500 Science > 540 Chemistry & allied sciences | ||||
| Status | Published | ||||
| Refereed | Yes, this version has been refereed | ||||
| Created at the University of Regensburg | Partially | ||||
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-543982 | ||||
| Item ID | 54398 |
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