4.8 Article

Highly Efficient Oxidation of Amines to Imines by Singlet Oxygen and Its Application in Ugi-Type Reactions

Journal

ORGANIC LETTERS
Volume 11, Issue 20, Pages 4568-4571

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol9018166

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Funding

  1. The University of Hong Kong
  2. University Grants Council [AoE 10/01P]

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A variety of secondary benzylic amines; were oxidized to imines in 90% to >99% yields by singlet oxygen generated from oxygen and a porphyrin photosensitizer. On the basis of these reactions, a protocol was developed for oxidative Ugi-type reactions with singlet oxygen as the oxidant. This protocol has been used to synthesize C1(-) and N-functionalized benzylic amines in up to 96% yields.

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