Abstract
The synthesis of new vicinal diamines based on aziridine and azetidine cores as well as the comparison of their catalytic activities as ligand in the Suzuki-Miyaura coupling reaction are described in this communication. The synthesis of three- and four-membered ring heterocycles substituted by a methylamine pendant arm is detailed from the parent nitrile derivatives. Complexation to palladium under various conditions has been examined affording vicinal diamines or amine-imidate complexes. The efficiency of four new catalytic systems is compared in the preparation of variously substituted biaryls. Aziridine- and azetidine-based catalytic systems allowed Suzuki-Miyaura reactions from aryl halides including chlorides with catalytic loadings until 0.001% at temperatures ranging from 100 °C to r.t. The evolution of the Pd-metallacycle ring strain moving from azetidine to aziridine in combination with a methylamine or an imidate pendant arm impacted the Suzuki-Miyaura reaction issue.
Highlights
The Suzuki-Miyaura reaction is “an easy way for C–C bonding” [1]
We describe new ligands based on strained aza‐heterocycles such as aziridines cycloalkylamines such as piperidines have been successfully developed in recent years [17,18,19,20,21,22,23]
Two new families of ligands based on an aziridine and azetidine core have been developed
Summary
The Suzuki-Miyaura reaction is “an easy way for C–C bonding” [1]. This statement is especially worthwhile in modern organic synthesis. The advent of the Suzuki-Miyaura reaction represents a critical step in this field. This reaction has become for decades a major methodological tool available to chemists to build molecular architectures especially based on a biaryl scaffold. If the formation of a biphenyl motif belongs nowadays to a textbook knowledge, the past decade has witnessed spectacular innovations and improvements such as ligandless transformations [10], supported or nanostructured catalytic systems [11,12,13], performing additives [14,15], neat and/or aqueous conditions [2,13,15], MW activations [10] for example
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