Journal
SYNTHESIS-STUTTGART
Volume 48, Issue 17, Pages 2795-2807Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0035-1562342
Keywords
nickel; Suzuki-Miyaura cross-coupling; quantitative; aryl chlorides; aryl bromides; aryl fluorides; aryl mesylates
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Funding
- National Science Foundation [DMR-1066116, DMR-1120901, OISE-1243313]
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [1066116] Funding Source: National Science Foundation
- Office Of The Director
- Office Of Internatl Science &Engineering [1243313] Funding Source: National Science Foundation
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Three classes of Ni precatalysts based on pi-Ni-II, pi-Ni-0 and sigma-Ni-II complexes have been elaborated and employed in different laboratories for the functionalization and cross-coupling of otherwise inert aryl C-O, C-Cl, and C-F electrophiles. Various Ni precatalysts, ligands, boron sources, and reaction conditions that were developed in various research groups, necessitated the selection of the most suitable conditions for desired cross-coupling partners. Here a universal, bench-stable, easily prepared (NiCl)-Cl-II(1-naphthyl)(PCy3)(2)/PCy3 sigma-complex, for efficient and quantitative cross-coupling of aryl chlorides, bromides, iodides, mesylates, and fluorides with aryl neopentylglycolboronates is reported. This precatalyst will most probably help to advance the applications of Ni catalysis in organic, supramolecular, and macromolecular synthesis and will provide an easier access to the selection of reaction conditions for various transformations.
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