Document Detail


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.
MedLine Citation:
PMID:  23881797     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Tao Wang; Shuai Shi; Mie Højer Vilhelmsen; Tuo Zhang; Matthias Rudolph; Frank Rominger; A Stephen K Hashmi
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-7-23
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  -     ISSN:  1521-3765     ISO Abbreviation:  Chemistry     Publication Date:  2013 Jul 
Date Detail:
Created Date:  2013-7-24     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-54-4205.
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