The metal-free cis selectiveh ydrogenation of alkynes catalyzed by ab oroxypyridine is reported. Av ariety of internala lkynesa re hydrogenated at 80 8Cu nder 5bar H 2 with good yields and stereoselectivity.F urthermore, the catalyst describedherein enablest he first metal-free semihydrogenation of terminal alkynes. Mechanistic investigations, substantiated by DFT computations, reveal that the mode of action by which the boroxypyridinea ctivates H 2 is reminiscent of the reactivity of an intramolecular frustratedL ewis pair.H owever,i ti st he change in the coordination mode of the boroxypyridine upon H 2 activationt hat allows the dissociationo ft he formedp yridone borane complex and subsequenthydroboration of an alkyne. This change in the coordinationm ode upon bond activation is described by the term boron-ligand cooperation.
We herein report the reaction of arylallenes with tris(pentafluorophenyl)borane that yields pentafluorophenyl substituted indens. The tris(pentafluorophenyl)borane induces the cyclization of the allene and transfers a pentafluorophenyl ring in the course...
We have developed a synthesis of 1,2-substituted adamantane carboxylic acids and further bridged cycloalkanes (cage compounds) by palladium acetate-catalyzed C-H bond oxidation. Acetoxylation of cycloalkane framework was performed using picolylamide as a directing group. Modification of the substrate, ligand design and variation of reaction conditions enabled us to study the mechanism of acetoxylation of aliphatic compounds. Post-functionalization reactions and cleavage of the directing group were developed. For the first time the synthesis and characterization of a β-C -tri-substituted adamantane derivatives was achieved.
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