Premium
A Nickel‐Catalyzed Carbonyl‐Heck Reaction
Author(s) -
Vandavasi Jaya Kishore,
Hua XiYe,
Halima Hamdi Ben,
Newman Stephen G.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201710241
Subject(s) - chemistry , heck reaction , catalysis , aldehyde , olefin fiber , reactivity (psychology) , ligand (biochemistry) , combinatorial chemistry , coupling reaction , nickel , ketone , amine gas treating , organic synthesis , intermolecular force , molecule , organic chemistry , palladium , medicine , biochemistry , alternative medicine , receptor , pathology
The use of transition‐metal catalysis to enable the coupling of readily available organic molecules has greatly enhanced the ability of chemists 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 π bond of the aldehyde takes the role of the olefin in the insertion/elimination steps.