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Organocatalytic β-Azidation of Enones Initiated by an Electron-Donor-Acceptor Complex.

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An operationally straightforward organocatalytic β-azidation of α,β-unsaturated ketones is described. Reaction of the Zhdankin azidoiodane with enones in the presence of a catalytic amount of an amine provides β-azido ketones… Click to show full abstract

An operationally straightforward organocatalytic β-azidation of α,β-unsaturated ketones is described. Reaction of the Zhdankin azidoiodane with enones in the presence of a catalytic amount of an amine provides β-azido ketones via the formation of an electron-donor-acceptor complex. The application of this protocol is demonstrated through one-step elaborations leading to the synthesis of unprecedented classes of 1,2,3-triazoles.

Keywords: acceptor complex; electron donor; organocatalytic azidation; donor acceptor

Journal Title: Organic letters
Year Published: 2017

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