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- Title
Chemoselectivity Control: Gold(I)-Catalyzed Synthesis of 6,7-Dihydrobenzofuran-4(5 H)-ones and Benzofurans from 1-(Alkynyl)-7-oxabicyclo[4.1.0]heptan-2-ones.
- Authors
Wang, Tao; Shi, Shuai; Vilhelmsen, Mie Højer; Zhang, Tuo; Rudolph, Matthias; Rominger , Frank; Hashmi , A. Stephen K.
- Abstract
New and chemoselective gold(I)-catalyzed transformations of 1-(arylethynyl)-7-oxabicyclo[4.1.0]- heptan-2-ones were developed. Two completely different products-6,7-dihydrobenzofuran-4(5 H)-ones and benzofurans-could be obtained from the same starting material. The selectivity is determined by the ligand of the gold catalyst: triphenylphosphine delivers 6,7-dihydrobenzofuran-4(5 H)-ones, and 1,3-bis(diisopropylphenyl)imidazol-2-ylidene leads to benzofurans. Eleven examples of each case are provided. The mechanistic suggestions for the pathways to both product types are supported by isotope labeling experiments.
- Subjects
CHEMOSELECTIVITY; GOLD catalysts; BENZOFURAN synthesis; HEPTANE; ALKYNE synthesis
- Publication
Chemistry - A European Journal, 2013, Vol 19, Issue 37, p12512
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201301698