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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
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
id
3c885513-2cb9-4780-ba22-030534847cad (old id 1694040)
date added to LUP
2010-10-27 14:09:51
date last changed
2018-05-29 09:34:09
@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},
  volume       = {51},
  year         = {2010},
}