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Aromatic allylation via diazotization: Metal-free C-C bond formation

Ek, Fredrik LU ; Axelsson, O; Wistrand, LG and Frejd, Torbjörn LU (2002) In Journal of Organic Chemistry 67(18). p.6376-6381
Abstract
A new method for the synthesis of allyl aromatic compounds not involving any metal-containing reagent or catalyst has been developed. Arylamines substituted with a large number of different substituents were converted via diazotizative deamination with tert-butyl nitrite in allyl bromide and acetonitrile to the corresponding allyl aromatic compounds. The allylation reaction was found to be suitable for larger scale synthesis due to short reaction times, a nonextractive workup, and robustness toward moisture, air, and type of solvent.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
67
issue
18
pages
6376 - 6381
publisher
The American Chemical Society
external identifiers
  • pmid:12201757
  • wos:000177880900013
  • scopus:0037031672
ISSN
1520-6904
DOI
10.1021/jo0258103
language
English
LU publication?
yes
id
514c2510-927d-4592-bbc8-884d67457141 (old id 329122)
date added to LUP
2007-08-02 16:44:10
date last changed
2017-07-30 03:44:50
@article{514c2510-927d-4592-bbc8-884d67457141,
  abstract     = {A new method for the synthesis of allyl aromatic compounds not involving any metal-containing reagent or catalyst has been developed. Arylamines substituted with a large number of different substituents were converted via diazotizative deamination with tert-butyl nitrite in allyl bromide and acetonitrile to the corresponding allyl aromatic compounds. The allylation reaction was found to be suitable for larger scale synthesis due to short reaction times, a nonextractive workup, and robustness toward moisture, air, and type of solvent.},
  author       = {Ek, Fredrik and Axelsson, O and Wistrand, LG and Frejd, Torbjörn},
  issn         = {1520-6904},
  language     = {eng},
  number       = {18},
  pages        = {6376--6381},
  publisher    = {The American Chemical Society},
  series       = {Journal of Organic Chemistry},
  title        = {Aromatic allylation via diazotization: Metal-free C-C bond formation},
  url          = {http://dx.doi.org/10.1021/jo0258103},
  volume       = {67},
  year         = {2002},
}