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HCl/DMF for enhanced chemoselectivity in catalytic hydrogenolysis reactions

Ochocinska, Agata LU ; Siegbahn, Anna LU and Ellervik, Ulf LU (2010) In Tetrahedron Letters 51(39). p.5200-5202
Abstract
An improved, chemoselective hydrogenolysis method has been developed. By employing a solvent-acid combination (i.e., DMF-aq HCl) we were able to favor debenzylation rather than aromatic hydrogenation and acid-mediated bond cleavage which are the two main drawbacks of these reactions. The generality of the method, which was primarily developed as a solution to a carbohydrate problem, is shown by the successful hydrogenolysis of 1,8-naphthalide, a previously unsolved problem. (C) 2010 Elsevier Ltd. All rights reserved.
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author
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron Letters
volume
51
issue
39
pages
5200 - 5202
publisher
Elsevier
external identifiers
  • wos:000282150800026
  • scopus:77956231314
ISSN
0040-4039
DOI
10.1016/j.tetlet.2010.07.142
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
3c885513-2cb9-4780-ba22-030534847cad (old id 1694040)
date added to LUP
2016-04-01 13:51:42
date last changed
2022-01-27 21:32:41
@article{3c885513-2cb9-4780-ba22-030534847cad,
  abstract     = {{An improved, chemoselective hydrogenolysis method has been developed. By employing a solvent-acid combination (i.e., DMF-aq HCl) we were able to favor debenzylation rather than aromatic hydrogenation and acid-mediated bond cleavage which are the two main drawbacks of these reactions. The generality of the method, which was primarily developed as a solution to a carbohydrate problem, is shown by the successful hydrogenolysis of 1,8-naphthalide, a previously unsolved problem. (C) 2010 Elsevier Ltd. All rights reserved.}},
  author       = {{Ochocinska, Agata and Siegbahn, Anna and Ellervik, Ulf}},
  issn         = {{0040-4039}},
  language     = {{eng}},
  number       = {{39}},
  pages        = {{5200--5202}},
  publisher    = {{Elsevier}},
  series       = {{Tetrahedron Letters}},
  title        = {{HCl/DMF for enhanced chemoselectivity in catalytic hydrogenolysis reactions}},
  url          = {{http://dx.doi.org/10.1016/j.tetlet.2010.07.142}},
  doi          = {{10.1016/j.tetlet.2010.07.142}},
  volume       = {{51}},
  year         = {{2010}},
}