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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
; ; and
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 (ACS)
external identifiers
  • pmid:12201757
  • wos:000177880900013
  • scopus:0037031672
ISSN
1520-6904
DOI
10.1021/jo0258103
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Chemical Biology and Drug Discovery (013210700)
id
514c2510-927d-4592-bbc8-884d67457141 (old id 329122)
date added to LUP
2016-04-01 12:11:24
date last changed
2022-01-27 00:04:16
@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 (ACS)}},
  series       = {{Journal of Organic Chemistry}},
  title        = {{Aromatic allylation via diazotization: Metal-free C-C bond formation}},
  url          = {{http://dx.doi.org/10.1021/jo0258103}},
  doi          = {{10.1021/jo0258103}},
  volume       = {{67}},
  year         = {{2002}},
}