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On the Reactivity of Phosphaalumenes towards C−C Multiple Bonds
2023, Nees, Samuel, Wellnitz, Tim, Dankert, Fabian, Härterich, Marcel, Dotzauer, Simon, Feldt, Milica, Braunschweig, Holger, Hering‐Junghans, Christian
Heterocycles containing group 13 and 15 elements such as borazines are an integral part of organic, biomedical and materials chemistry. Surprisingly, heterocycles containing P and Al are rare. We have now utilized phosphaalumenes in reactions with alkynes, alkenes and conjugated double bond systems. With sterically demanding alkynes 1,2-phosphaalumetes were afforded, whereas the reaction with HCCH or HCCSiMe3 gave 1,4-phosphaaluminabarrelenes. Using styrene saturated 1,2-phosphaalumates were formed, which reacted further with additional styrene to give different regio-isomers of 1,4-aluminaphosphorinanes. Using ethylene, a 1,4-aluminaphosphorinane is obtained, while with 1,3-butadiene a bicyclic system containing an aluminacyclopentane and a phosphirane unit was synthesized. The experimental work is supported by theoretical studies to shed light on the mechanism governing the formation of these heterocycles.
Novel naphthylpyridines from cobalt-catalyzed cyclotrimerization of a chiral diyne
2017-11-28, Trommer, Volkmar, Fischer, Fabian, Hapke, Marko
The concise synthesis of a novel chiral diyne substrate for the assembly of chiral naphthylpyridines was described and different conditions for the cobalt-catalyzed co-cyclotrimerization with nitriles investigated. The products are novel naphthylpyridines possessing configurationally stable biaryl axes.