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Comparison of dppf‐Supported Nickel Precatalysts for the Suzuki–Miyaura Reaction: The Observation and Activity of Nickel(I)
Author(s) -
Guard Louise M.,
Mohadjer Beromi Megan,
Brudvig Gary W.,
Hazari Nilay,
Vinyard David J.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201505699
Subject(s) - nickel , chemistry , catalysis , ligand (biochemistry) , combinatorial chemistry , reaction conditions , organic chemistry , biochemistry , receptor
Abstract Ni‐based precatalysts for the Suzuki–Miyaura reaction have potential chemical and economic advantages compared to commonly used Pd systems. Here, we compare Ni precatalysts for the Suzuki–Miyaura reaction supported by the dppf ligand in 3 oxidation states, 0, I and II. Surprisingly, at 80 °C they give similar catalytic activity, with all systems generating significant amounts of Ni I during the reaction. At room temperature a readily accessible bench‐stable Ni II precatalyst is highly active and can couple synthetically important heterocyclic substrates. Our work conclusively establishes that Ni I species are relevant in reactions typically proposed to involve exclusively Ni 0 and Ni II complexes.