期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 49, 页码 14898-14902出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201507369
关键词
catalysis; heterocycles; photocatalysis; radical reactions; rearrangement
资金
- Eli Lilly and Company
- NIH-NIGMS [R01-GM096129]
- Camille Dreyfus Teacher-Scholar Award Program
- Eli Lilly
- University of Michigan
- National Science Foundation [DGE 1256260]
A visible-light-mediated radical Smiles rearrangement has been developed to address the challenging synthesis of the gem-difluoro group present in an opioid receptor-like 1 (ORL-1) antagonist that is currently in development for the treatment of depression and/or obesity. This method enables the direct and efficient introduction of the difluoroethanol motif into a range of aryl and heteroaryl systems, representing a new disconnection for the synthesis of this versatile moiety. When applied to the target compound, the photochemical step could be conducted on 15 g scale using industrially relevant [Ru(bpy)(3)Cl-2] catalyst loadings of 0.01 mol%. This transformation is part of an overall five-step route to the antagonist that compares favorably to the current synthetic sequence and demonstrates, in this specific case, a clear strategic benefit of photocatalysis.
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