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Pd(II)-catalyzed hydroxyl-directed C-H olefination enabled by monoprotected amino acid ligands

Academic Article
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Overview

related to degree

  • Engle, Keary M., Ph.D. in Chemistry, Scripps Research 2008 - 2013
  • Wang, Donghui, Ph.D., Scripps Research , transferred from Brandeis Univeristy 2007 - 2010

authors

  • Lu, Y.
  • Wang, Donghui
  • Engle, Keary M.
  • Yu, Jin-Quan

publication date

  • April 2010

journal

  • Journal of the American Chemical Society  Journal

abstract

  • A novel Pd(II)-catalyzed ortho-C-H olefination protocol has been developed using spatially remote, unprotected tertiary, secondary, and primary alcohols as the directing groups. Mono-N-protected amino acid ligands were found to promote the reaction, and an array of olefin coupling partners could be used. When electron-deficient alkenes were used, the resulting olefinated intermediates underwent subsequent Pd(II)-catalyzed oxidative intramolecular cyclization to give the corresponding pyran products, which could be converted into ortho-alkylated alcohols under hydrogenolysis conditions. The mechanistic details of the oxidative cyclization step are discussed and situated in the context of the overall catalytic cycle.

subject areas

  • Alkenes
  • Amino Acids
  • Carbon
  • Catalysis
  • Hydrogen
  • Hydroxides
  • Ligands
  • Palladium
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Identity

PubMed Central ID

  • PMC2882203

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja101909t

PubMed ID

  • 20359184
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Additional Document Info

start page

  • 5916

end page

  • 5921

volume

  • 132

issue

  • 16

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