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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Highly Ambiphilic Room Temperature Stable Six-Membered Cyclic (Alkyl)(amino)carbenes
Cory M Weinstein1, Glen P Junor1, Daniel R Tolentino1
1UCSD-CNRS Joint Research Laboratory (UMI 3555), Department of Chemistry and Biochemistry , University of California, San Diego , La Jolla , California 92093-0358 , United States.
Abstract:
Cyclic (alkyl)(amino)carbenes with a six-membered backbone were prepared. Compared to their five-membered analogues, they feature increased % Vbur and enhanced donor and acceptor properties, as evidenced by the observed n → π* transition trailing into the visible region. The high ambiphilic character even allows for the intramolecular insertion of the carbene into an unactivated C(sp3)-H bond. When used as ligands, they outcompete the five-membered analogues in the palladium-mediated α-arylation of ketones with aryl chlorides.
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