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Disclosed herein is a novel, redox-neutral protocol for the visible-light-induced radical alkynylation of unactivated olefins. The intramolecular migration of an alkynyl group, by cleaving an inert C−C σ bond, is realized for the first time. A wide range of synthetically useful trifluoroethylated linear alkynes are readily obtained under mild reaction conditions. [ABSTRACT FROM AUTHOR]

The first iridium-catalyzed intermolecular cyclization between alkynes and ring-fused benzocyclobutenols (RBCB) through C--C bond cleavage is described. A variety of elusive polycyclic aromatic hydrocarbons (PAHs) with multiple substituents are obtained in good yields under mild conditions. This procedure provides a unique and expeditious tool for the synthesis of PAHs. [ABSTRACT FROM AUTHOR]

A novel, manganese-catalyzed oxidative azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in synthetically useful yields and exclusive regioselectivity. Aside from linear alkyl azides, otherwise elusive medium-sized cyclic azides were also readily prepared. Preliminary mechanistic studies reveal that the reaction likely proceeds by a radical-mediated CC bond cleavage/CN3 bond formation pathway. [ABSTRACT FROM AUTHOR]