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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
; ; and
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
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)
id
d06d4512-1c3a-4ff4-bb61-2bde32bb08e4 (old id 411326)
date added to LUP
2016-04-01 15:37:42
date last changed
2022-02-27 07:57:39
@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}},
  keywords     = {{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}},
  doi          = {{10.1055/s-2006-926371}},
  year         = {{2006}},
}