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Gold α-Oxo Carbenoids in Catalysis: Catalytic Oxygen-Atom Transfer to Alkynes.
MedLine Citation:
PMID:  21726021     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
An overview of reactive gold α-oxo carbenoid intermediates in the gold-catalyzed functionalization of alkynes is presented. Such intermediates can be generated from inter- and intramolecular oxidation of alkynes by nucleophilic oxygen-atom donor groups, such as amine N-oxides, pyridine N-oxides, nitrones, nitro compounds, sulfoxides, and epoxides. These O-atom transfer processes occur by gold-mediated addition-elimination reactions. In catalytic systems, α-oxo carbenoids can undergo nucleophilic attack by imine, arene, and migrating hydride as well as alkyl groups, leading to cascade reactions and the construction of new skeletons. The facile construction of CE (E=C, N, S, or O) bonds makes it an attractive step-economic approach to value-added molecules from readily available starting materials. The scope, mechanisms, and reactivity of such α-oxo carbenoid species are discussed. The remarkable diversity of structures accessible is demonstrated with various recent examples.
Authors:
Jian Xiao; Xingwei Li
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-7-1
Journal Detail:
Title:  Angewandte Chemie (International ed. in English)     Volume:  -     ISSN:  1521-3773     ISO Abbreviation:  -     Publication Date:  2011 Jul 
Date Detail:
Created Date:  2011-7-4     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0370543     Medline TA:  Angew Chem Int Ed Engl     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Dalian Institute of Chemical Physics, The Chinese Academy of Sciences, Dalian, 116023 (P. R. China), Fax: (+86) 411-8437-9089.
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