HCl/DMF for enhanced chemoselectivity in catalytic hydrogenolysis reactions

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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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Ämnesklassifikation (UKÄ) – OBLIGATORISK

  • Organisk kemi
Originalspråkengelska
Sidor (från-till)5200-5202
TidskriftTetrahedron Letters
Volym51
Utgivningsnummer39
StatusPublished - 2010
PublikationskategoriForskning
Peer review utfördJa