Transition-metal-free amine oxidation: a chemoselective strategy for the late-stage formation of lactams

Robert J. Griffiths, Glenn A. Burley, Eric P.A. Talbot

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A metal-free strategy for the formation of lactams via selective oxidation of cyclic secondary and tertiary amines is described. Molecular iodine facilitates both chemoselective and regioselective oxidation of C–H bonds directly adjacent to a cyclic amine. The mild conditions, functional group tolerance, and substrate scope are demonstrated using a suite of diverse small molecule cyclic amines, including clinically approved drug scaffolds.
LanguageEnglish
Pages870-873
JournalOrganic Letters
Volume19
Issue number4
DOIs
Publication statusPublished - 8 Feb 2017

Fingerprint

Lactams
Amines
Transition metals
amines
Metals
transition metals
Oxidation
oxidation
Scaffolds
Iodine
Functional groups
iodine
drugs
Molecules
Substrates
Pharmaceutical Preparations
metals
molecules

Keywords

  • metal-free
  • amine oxidation
  • lactams
  • iodine
  • drug scaffolds

Cite this

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abstract = "A metal-free strategy for the formation of lactams via selective oxidation of cyclic secondary and tertiary amines is described. Molecular iodine facilitates both chemoselective and regioselective oxidation of C–H bonds directly adjacent to a cyclic amine. The mild conditions, functional group tolerance, and substrate scope are demonstrated using a suite of diverse small molecule cyclic amines, including clinically approved drug scaffolds.",
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Transition-metal-free amine oxidation : a chemoselective strategy for the late-stage formation of lactams. / Griffiths, Robert J.; Burley, Glenn A.; Talbot, Eric P.A.

In: Organic Letters, Vol. 19, No. 4, 08.02.2017, p. 870-873.

Research output: Contribution to journalArticle

TY - JOUR

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T2 - Organic Letters

AU - Griffiths, Robert J.

AU - Burley, Glenn A.

AU - Talbot, Eric P.A.

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AB - A metal-free strategy for the formation of lactams via selective oxidation of cyclic secondary and tertiary amines is described. Molecular iodine facilitates both chemoselective and regioselective oxidation of C–H bonds directly adjacent to a cyclic amine. The mild conditions, functional group tolerance, and substrate scope are demonstrated using a suite of diverse small molecule cyclic amines, including clinically approved drug scaffolds.

KW - metal-free

KW - amine oxidation

KW - lactams

KW - iodine

KW - drug scaffolds

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