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Ligand-enabled γ-C(sp(3))-H olefination of amines: en route to pyrrolidines

Academic Article
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Overview

related to degree

  • Liu, Tao, Ph.D. in Chemistry, Scripps Research 2013 - 2018
  • He, Jian, Ph.D. in Chemistry, Scripps Research 2011 - 2016

authors

  • Jiang, H.
  • He, Jian
  • Liu, Tao
  • Yu, Jin-Quan

publication date

  • February 2016

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Pd(II)-catalyzed olefination of ?-C(sp(3))-H bonds of triflyl (Tf) and 4-nitrobenzenesulfonyl (Ns) protected amines is achieved. Subsequent aza-Wacker oxidative cyclization or conjugate addition of the olefinated intermediates provides a variety of C-2 alkylated pyrrolidines. Three pyridine- and quinoline-based ligands are developed to match different classes of amine substrates, demonstrating a rare example of ligand-enabled C(sp(3))-H olefination reactions. The use of Ns protecting group to direct C(sp(3))-H activation of alkyl amines is also a significant step toward practical C-H functionalizations of alkyl amines.
  • Pd(II)-catalyzed olefination of γ-C(sp(3))-H bonds of triflyl (Tf) and 4-nitrobenzenesulfonyl (Ns) protected amines is achieved. Subsequent aza-Wacker oxidative cyclization or conjugate addition of the olefinated intermediates provides a variety of C-2 alkylated pyrrolidines. Three pyridine- and quinoline-based ligands are developed to match different classes of amine substrates, demonstrating a rare example of ligand-enabled C(sp(3))-H olefination reactions. The use of Ns protecting group to direct C(sp(3))-H activation of alkyl amines is also a significant step toward practical C-H functionalizations of alkyl amines.

subject areas

  • Alkenes
  • Amines
  • Chelating Agents
  • Ferrous Compounds
  • Ligands
  • Palladium
  • Pyrrolidines
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Identity

PubMed Central ID

  • PMC4817546

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/jacs.5b13462

PubMed ID

  • 26796676
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Additional Document Info

start page

  • 2055

end page

  • 2059

volume

  • 138

issue

  • 6

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