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Desaturation of a hydrocarbon by direct H2-transfer

A team of researchers in Professor Thomas Hoye's laboratories, composed of Dawen Niu, Pat Willoughby, Brian Woods and Beeru Baire, has uncovered a new type of transformation. They reported last week in Nature (doi:10.1038/nature12492) that reactive benzyne derivatives, formed by the hexadehydro-Diels-Alder (HDDA) reaction (doi:10.1038/nature11518), will abstract two hydrogen atoms from a saturated alkane to produce the corresponding alkene (via oxidation) and benzenoid (via reduction) disproportionation products. Mechanistic and computational studies all point to the involvement of a concerted dihydrogen transfer event via a planar transition structure geometry. The investigators comment, "We are not aware of any single-step, bimolecular reaction in which two hydrogen atoms are simultaneously transferred from a saturated alkane."1

1. "Alkane desaturation by concerted double hydrogen atom transfer to benzyne," Niu, D.; Willoughby, P. H.; Baire, B.; Woods, B. P.; Hoye, T. R. Nature 2013, 501, 531-534. (doi:10.1038/nature12492)