3 years ago

A Nickel-Catalyzed Carbonyl-Heck Reaction

XiYe Hua, Hamdi Ben Halima, Jaya Kishore Vandavasi, Stephen G. Newman
The use of transition metal catalysis to enable the coupling of readily available organic molecules has greatly enhanced the chemist's ability to access complex chemical structures. In this work, an intermolecular coupling reaction that unites organotriflates and aldehydes is presented. A unique catalyst system is identified to enable this reaction, featuring a Ni(0) precatalyst, a tridentate Triphos ligand, and a bulky amine base. This transformation provides access to a variety of ketone-containing products without the selectivity and reactivity-related challenges associated with more traditional Friedel-Crafts reactions. A Heck-type mechanism is postulated, wherein the pi-bond of the aldehyde takes the role of the olefin in the insertion/elimination steps.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201710241

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