Synthesis 2016; 48(17): 2795-2807
DOI: 10.1055/s-0035-1562342
special topic
© Georg Thieme Verlag Stuttgart · New York

An Indefinitely Air-Stable σ-NiII Precatalyst for Quantitative Cross-Coupling of Unreactive Aryl Halides and Mesylates with Aryl Neopentylglycolboronates

Jagadeesh Malineni
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA   Email: percec@sas.upenn.edu
,
Ryan L. Jezorek
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA   Email: percec@sas.upenn.edu
,
Na Zhang
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA   Email: percec@sas.upenn.edu
,
Virgil Percec*
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA   Email: percec@sas.upenn.edu
› Author Affiliations
Further Information

Publication History

Received: 22 April 2016

Accepted after revision: 23 May 2016

Publication Date:
28 June 2016 (eFirst)

Abstract

Three classes of Ni precatalysts based on π-NiII, π-Ni0 and σ-NiII 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 NiIICl(1-naphthyl)(PCy3)2/PCy3 σ-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.

Supporting Information

 
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