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Chemoselectivity control: gold(I)-catalyzed synthesis of 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans from 1-(alkynyl)-7-oxabicyclo[4.1.0]heptan-2-ones

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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(5H)-ones and benzofurans—could be obtained from the same starting material. The selectivity is determined by the li...

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Bibliographic Details
Main Authors: Wang, Tao (Author) , Shi, Shuai (Author) , Larsen, Mie Højer (Author) , Zhang, Tuo (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: July 23, 2013
In: Chemistry - a European journal
Year: 2013, Volume: 19, Issue: 37, Pages: 12512-12516
ISSN:1521-3765
DOI:10.1002/chem.201301698
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201301698
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201301698
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Author Notes:Tao Wang, Shuai Shi, Mie Højer Vilhelmsen, Tuo Zhang, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
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Summary: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(5H)-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(5H)-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.
Item Description:Gesehen am 30.09.2021
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201301698

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