Catalytic intermolecular hydroaminations of unactivated olefins with secondary alkyl amines

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Science  17 Feb 2017:
Vol. 355, Issue 6326, pp. 727-730
DOI: 10.1126/science.aal3010

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Hydroamination gets a light push uphill

Hydroamination of olefins is a broadly useful method for making carbon-nitrogen bonds. However, when both the amine and the olefin have multiple alkyl substituents, the reaction can become energetically unfavorable. Musacchio et al. used the energy in blue light to surmount this obstacle (see the Perspective by Buchanan and Hull). A photo-excited iridium complex oxidized the amine, which in turn bonded efficiently to the olefin, after which a thiophenol cocatalyst shuttled the electron back. The reaction could operate across a wide range of amine and olefin partners.

Science, this issue p. 727; see also p. 690