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Selective synthesis of 2-substituted pyridine N-oxides via directed ortho-metallation using Grignard reagents

Andersson, Hans ; Gustafsson, Magnus LU ; Olsson, Roger LU orcid and Almqvist, Fredrik (2008) In Tetrahedron Letters 49(48). p.6901-6903
Abstract

Addition of i-PrMgCl to pyridine N-oxides in THF at -78 °C generates selectively an ortho-metallated species, which can be trapped with various electrophiles to generate 2-substituted pyridine N-oxides. Furthermore, by applying a double metal-catalyzed cross-coupling, direct arylation of the pyridine N-oxides is achieved.

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author
; ; and
publishing date
type
Contribution to journal
publication status
published
in
Tetrahedron Letters
volume
49
issue
48
pages
6901 - 6903
publisher
Elsevier
external identifiers
  • scopus:53549097051
ISSN
0040-4039
DOI
10.1016/j.tetlet.2008.09.104
language
English
LU publication?
no
id
7bf47b1c-0112-4427-bfb4-852811b29ba3
date added to LUP
2019-10-02 10:20:43
date last changed
2022-02-16 00:20:15
@article{7bf47b1c-0112-4427-bfb4-852811b29ba3,
  abstract     = {{<p>Addition of i-PrMgCl to pyridine N-oxides in THF at -78 °C generates selectively an ortho-metallated species, which can be trapped with various electrophiles to generate 2-substituted pyridine N-oxides. Furthermore, by applying a double metal-catalyzed cross-coupling, direct arylation of the pyridine N-oxides is achieved.</p>}},
  author       = {{Andersson, Hans and Gustafsson, Magnus and Olsson, Roger and Almqvist, Fredrik}},
  issn         = {{0040-4039}},
  language     = {{eng}},
  month        = {{11}},
  number       = {{48}},
  pages        = {{6901--6903}},
  publisher    = {{Elsevier}},
  series       = {{Tetrahedron Letters}},
  title        = {{Selective synthesis of 2-substituted pyridine N-oxides via directed ortho-metallation using Grignard reagents}},
  url          = {{http://dx.doi.org/10.1016/j.tetlet.2008.09.104}},
  doi          = {{10.1016/j.tetlet.2008.09.104}},
  volume       = {{49}},
  year         = {{2008}},
}