Aromatic allylation via diazotization: Metal-free C-C bond formation
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/329122
- author
- Ek, Fredrik LU ; Axelsson, O ; Wistrand, LG and Frejd, Torbjörn LU
- organization
- publishing date
- 2002
- 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}}, }