N-heterocyclic carbene–palladium catalysts for the bisdiene cyclization-trapping reaction with sulfonamides under thermal and microwave conditions

作者: James M. Takacs , Somasundaram Venkataraman , Ross N. Andrews , Libbie S.W. Pelter

DOI: 10.1016/J.JORGANCHEM.2005.08.048

关键词:

摘要: Abstract Simple palladium-N-heterocyclic carbene catalysts readily effect the palladium-catalyzed cyclization-trapping of bisdienes with sulfonamides. The reaction is quite efficient for a variety sulfonamides and several bisdienes. For example, using 0.1% in situ generated or preformed (IMes)Pd(η 3 -C H 5 )Cl complex, simple bisdiene TsN(H)CH 2 Ph proceeds good yield under thermal conditions (74–75%, 75 °C, 9 h). same run microwave irradiation somewhat faster even higher (86%, 2.5 h).

参考文章(25)
Mihai S. Viciu, Oscar Navarro, Romain F. Germaneau, Roy A. Kelly, William Sommer, Nicolas Marion, Edwin D. Stevens, Luigi Cavallo, Steven P. Nolan, Synthetic and Structural Studies of (NHC)Pd(allyl)Cl Complexes (NHC = N-heterocyclic carbene) Organometallics. ,vol. 23, pp. 1629- 1635 ,(2004) , 10.1021/OM034319E
Yoshio Inoue, Masaaki Taguchi, Masanori Toyofuku, Harukichi Hashimoto, N-allylation of imides catalyzed by palladium(0). Bulletin of the Chemical Society of Japan. ,vol. 57, pp. 3021- 3022 ,(1984) , 10.1246/BCSJ.57.3021
Andrew J. McCarroll, David A. Sandham, Lisa R. Titcomb, Alexandra K. de K. Lewis, F. Geoffrey N. Cloke, Brian P. Davies, Alejandro Perez de Santana, Wolfgang Hiller, Stephen Caddick, Studies on high-temperature amination reactions of aromatic chlorides using discrete palladium-N-heterocyclic carbene (NHC) complexes and in situ palladium/imidazolium salt protocols. Molecular Diversity. ,vol. 7, pp. 115- 123 ,(2003) , 10.1023/B:MODI.0000006863.14423.DA
Alois Fürstner, Frank Stelzer, Antonio Rumbo, Helga Krause, Total Synthesis of the Turrianes and Evaluation of Their DNA‐Cleaving Properties Chemistry: A European Journal. ,vol. 8, pp. 1856- 1871 ,(2002) , 10.1002/1521-3765(20020415)8:8<1856::AID-CHEM1856>3.0.CO;2-R
Gian Paolo Chiusoli, Mirco Costa, Luciano Pallini, Giuliana Terenghi, Transition metal-catalysed sequences of nucleophilic addition Transition Metal Chemistry. ,vol. 7, pp. 304- 306 ,(1982) , 10.1007/BF00618336
Ralf Jackstell, Surendra Harkal, Haijun Jiao, Anke Spannenberg, Cornelia Borgmann, Dirk Röttger, Franz Nierlich, Mark Elliot, Stuart Niven, Kingsley Cavell, Oscar Navarro, Mihai S. Viciu, Steven P. Nolan, Matthias Beller, An Industrially Viable Catalyst System for Palladium-Catalyzed Telomerizations of 1,3-Butadiene with Alcohols Chemistry: A European Journal. ,vol. 10, pp. 3891- 3900 ,(2004) , 10.1002/CHEM.200400182