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HCl/DMF for enhanced chemoselectivity in catalytic hydrogenolysis reactions

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Author

Summary, in English

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.

Publishing year

2010

Language

English

Pages

5200-5202

Publication/Series

Tetrahedron Letters

Volume

51

Issue

39

Document type

Journal article

Publisher

Elsevier

Topic

  • Organic Chemistry

Status

Published

ISBN/ISSN/Other

  • ISSN: 0040-4039