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Catalytic Use of Selenium Electrophiles in Cyclizations
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Abstract
A new and convenient one-pot method for a catalytic addition−elimination reaction using selenium electrophiles has been developed. In the presence of 5 mol % diphenyl diselenide, [bis(trifluoroacetoxy)iodo]benzene in acetonitrile converted a range of (E)-3-butenoic acids into the corresponding butenolides in good yields.
Citing Articles
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This article has been cited by 9 ACS Journal articles (5 most recent appear below).
Selenide Ions as Catalysts for Homo- and Crossed-Tishchenko Reactions of Expanded Scope
Simon P. Curran and Stephen J. ConnonOrganic Letters2012 Article ASAPSelenide Ions as Catalysts for Homo- and Crossed-Tishchenko Reactions of Expanded Scope
Simon P. Curran and Stephen J. ConnonOrganic Letters2012 Article ASAPSelenide ions have been shown to catalyze the Tishchenko reaction for the first time. These catalysts are superior to previously reported thiolate analogues and promote the disproportionation of aldehydes with increased reaction rates and broader scope at ...
Selenium-Catalyzed Regioselective Cyclization of Unsaturated Carboxylic Acids Using Hypervalent Iodine Oxidants
Fateh V. Singh and Thomas WirthOrganic Letters2011 13 (24), 6504-6507Selenium-Catalyzed Regioselective Cyclization of Unsaturated Carboxylic Acids Using Hypervalent Iodine Oxidants
Fateh V. Singh and Thomas WirthOrganic Letters2011 13 (24), 6504-6507A new and convenient selenium-catalyzed regioselective cyclization of γ,δ-unsaturated carboxylic acids to the corresponding 3,6-dihydro-2H-pyran-2-ones is described. The cyclization products have been obtained in good to excellent yields using diphenyl ...
FeCl3/NaI-Catalyzed Allylic C–H Oxidation of Arylalkenes with a Catalytic Amount of Disulfide under Air
Deshun Huang, Haining Wang, Fazhen Xue, and Yian ShiThe Journal of Organic Chemistry2011 Article ASAPFeCl3/NaI-Catalyzed Allylic C–H Oxidation of Arylalkenes with a Catalytic Amount of Disulfide under Air
Deshun Huang, Haining Wang, Fazhen Xue, and Yian ShiThe Journal of Organic Chemistry2011 Article ASAPThis paper describes a FeCl3/NaI-catalyzed formal allylic C–H oxidation of arylalkenes using a catalytic amount of disulfide with BnOH and 4-nitroaniline as nucleophiles and air as oxidant to form the corresponding allyl ethers and amines. A possible ...
An Acid-Catalyzed Formal Allylic C−H Oxidation of Aryl Cycloalkenes with N-Propylthiosuccinimide
Deshun Huang, Haining Wang, Huan Guan, Hu Huang, and Yian ShiOrganic Letters2011 13 (6), 1548-1551An Acid-Catalyzed Formal Allylic C−H Oxidation of Aryl Cycloalkenes with N-Propylthiosuccinimide
Deshun Huang, Haining Wang, Huan Guan, Hu Huang, and Yian ShiOrganic Letters2011 13 (6), 1548-1551A mild acid-catalyzed formal allylic C−H oxidation of aryl cycloalkenes with N-propylthiosuccinimide in the presence of various nucleophiles to generate allylic ethers, esters, and sulfonamides is described. A possible reaction mechanism has been ...
Organoselenium Chemistry: Role of Intramolecular Interactions
Anna J. Mukherjee, Sanjio S. Zade, Harkesh B. Singh and Raghavan B. SunojChemical Reviews2010 110 (7), 4357-4416Organoselenium Chemistry: Role of Intramolecular Interactions
Anna J. Mukherjee, Sanjio S. Zade, Harkesh B. Singh and Raghavan B. SunojChemical Reviews2010 110 (7), 4357-4416
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History
- Published In Issue August 02, 2007
- Received May 29, 2007
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