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- Title
Regio‐ and Stereoselective Vicinal syn‐Arylation‐Trifluoromethylation of Terminal Arylacetylenes.
- Authors
Xiao, Chang; Wan, Hai‐Xing; Zhang, Song‐Lin
- Abstract
One‐pot three‐component syn‐arylation‐trifluoromethylation of terminal arylalkynes is developed by using an isolated (phen)Cu(III)(CF3)3 complex (phen: phenanthroline) and aryl boronic acids. This reaction is chemoselective that can suppress the competing trifluoromethylation of alkyne C−H and aryl boronic acids. It is also regioselective to install an aryl group on Cα and a CF3 group on Cβ of arylalkynes. Finally, unusual syn‐difunctionalization chemistry is achieved that is complementary to the general anti‐stereochemistry for difunctionalization of alkynes involving trifluoromethylation. The use of a Cu(III)−CF3 complex is crucial to the success that not only acts as a reactive CF3 precursor, but is also responsible for the unusual syn‐stereochemistry. This study allows ready access to vicinal arylated‐trifluoromethylated olefins, which is a widely existing structural motif in many biologically active compounds.
- Subjects
BIOACTIVE compounds; BORONIC acids; ARYL group; CHEMOSELECTIVITY
- Publication
Asian Journal of Organic Chemistry, 2019, Vol 8, Issue 5, p654
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.201800432