4.8 Article

Redox-Neutral α-C-H Bond Functionalization of Secondary Amines with Concurrent C-P Bond Formation/N-Alkylation

Journal

ORGANIC LETTERS
Volume 15, Issue 17, Pages 4358-4361

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol401858k

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Funding

  1. NIH-NIGMS [R01GM101389-01]
  2. Amgen Young Investigator Award

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Redox-neutral formation of C-P bonds in the alpha-position of amines was achieved via a process that features a combination of an oxidative alpha-C-H bond functionalization and a reductive N-alkylation. Benzoic acid functions as an efficient catalyst in this three-component reaction of cyclic secondary amines, aldehydes and phosphine oxides to provide rapid access to alpha-amino phosphine oxides not easily accessible by classic Kabachnik-Fields reactions.

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