Recent Advances in the Application of SelectfluorTMF-TEDA-BF4 as a Versatile Mediator or Catalyst in Organic Synthesis 英文参考文献.docVIP

Molecules 2011, 16, 6432-6464; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Review Recent Advances in the Application of SelectfluorTMF-TEDA-BF4 as a Versatile Mediator or Catalyst in Organic Synthesis Stojan Stavber 1,2 1 Laboratory for Organic and Bioorganic Chemistry, “Jo?ef Stefan” Institute, Jamova 39, 1000 Ljubljana, Slovenia 2 Centre of Excellence CIPKeBiP, Jamova 39, 1000 Ljubljana, Slovenia; E-Mail: stojan.stavber@ijs.si; Tel.: +386-1-477-3660, Fax: +386-1-423-5400 Received: 14 June 2011; in revised form: 5 July 2011 / Accepted: 19 July 2011 / Published: 29 July 2011 Abstract: SelectfluorTM F-TEDA-BF4 (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [2.2.2]octane bis(tetrafluoroborate) is not only one of the most efficient and popular reagents for electrophilic fluorination, but as a strong oxidant is also a convenient mediator or catalyst of several “fluorine-free” functionalizations of organic compounds. Its applications as a mediator in transformations of oxidizable functional groups or gold-catalyzed C-C and C-heteroatom oxidative coupling reactions, a catalyst in formation of various heterocyclic rings, a reagent or catalyst of various functionalizations of electron-rich organic compounds (iodination, bromination, chlorination, nitration, thiocyanation, sulfenylation, alkylation, alkoxylation), a catalyst of one-pot-multi- component coupling reactions, a catalyst of regioselective ring opening of epoxides, a deprotection reagent for various protecting groups, and a mediator for stereoselective rearrangement processes of bicyclic compounds are reviewed and discussed. Keywords: SelectfluorTM F-TEDA-BF4; oxidative transformations; coupling reactions; halogenation 1. Introduction Selective fluorofunctionalisation of organic compounds under mild reaction conditions following an electrophilic