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Solvent-free Heck-Jeffery reactions under ball-milling conditions applied to the synthesis of unnatural amino acids precursors and Indoles

Tullberg, Erik LU ; Schacher, F; Peters, D and Frejd, Torbjörn LU (2006) In Synthesis p.1183-1189
Abstract
The syntheses of various amino- and hydroxy-substituted dehydrophenylalanine derivatives using the Heck-Jeffery protocol under non-solvent conditions in a ball mill are presented. The influences of electron-withdrawing groups and of the location of the heteroatom substituent relative to the halide are discussed. Suitably substituted ortho-amino dehydrophenylalanine derivatives undergo a cyclization-elimination reaction to the corresponding 2-substituted indoles.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
palladium, Heck reaction, green chemistry, cyclizations, indoles
in
Synthesis
issue
7
pages
1183 - 1189
publisher
Oxford Polytechnic, Oxford
external identifiers
  • wos:000236727200019
  • scopus:33645991539
ISSN
0039-7881
DOI
10.1055/s-2006-926371
language
English
LU publication?
yes
id
d06d4512-1c3a-4ff4-bb61-2bde32bb08e4 (old id 411326)
date added to LUP
2007-10-20 13:21:37
date last changed
2019-08-07 02:49:20
@article{d06d4512-1c3a-4ff4-bb61-2bde32bb08e4,
  abstract     = {The syntheses of various amino- and hydroxy-substituted dehydrophenylalanine derivatives using the Heck-Jeffery protocol under non-solvent conditions in a ball mill are presented. The influences of electron-withdrawing groups and of the location of the heteroatom substituent relative to the halide are discussed. Suitably substituted ortho-amino dehydrophenylalanine derivatives undergo a cyclization-elimination reaction to the corresponding 2-substituted indoles.},
  author       = {Tullberg, Erik and Schacher, F and Peters, D and Frejd, Torbjörn},
  issn         = {0039-7881},
  keyword      = {palladium,Heck reaction,green chemistry,cyclizations,indoles},
  language     = {eng},
  number       = {7},
  pages        = {1183--1189},
  publisher    = {Oxford Polytechnic, Oxford},
  series       = {Synthesis},
  title        = {Solvent-free Heck-Jeffery reactions under ball-milling conditions applied to the synthesis of unnatural amino acids precursors and Indoles},
  url          = {http://dx.doi.org/10.1055/s-2006-926371},
  year         = {2006},
}