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Flyer: Prof. Jack Norton Flyer
Title: Applications of Catalytic H• Transfer from H2
Abstract: Transition-metal hydride complexes with en-he bonds stronger than 56 kcal mol’ can often be generated from hydrogen, and may thus be able to catalyze the transfer of H from that gas. Hydrides with unusually weak M-H bonds, such as HV(CO),(dppe), can carry out stoichiometric cyclizations of enamines that contain a remote C=C, converting them to pyrrolidines. The reaction of a Co(Il) salen complex with an olefin in the presence of NaBH, and ‘BuOOH also appears to form a radical by H• transfer, and these radicals can be trapped by TEMPO. The photochemical oxidation of these TEMPO adducts to carbocations (Knowles, Angew. Chem. Int. Ed. 2016, 55, 9969) allows the interception of these cations by many different nucleophiles, giving Markovnikov hydrofunctionalization products. A particularly valuable application of this reaction is in the net hydrofluorination of olefins.
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