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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
Author(s) -
Wang Tao,
Shi Shuai,
Vilhelmsen Mie Højer,
Zhang Tuo,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301698
Subject(s) - chemoselectivity , catalysis , chemistry , triphenylphosphine , ligand (biochemistry) , combinatorial chemistry , selectivity , medicinal chemistry , organic chemistry , receptor , biochemistry
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.