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        Synthesis  2007(18): 2867-2871  
DOI: 10.1055/s-2007-983825
   DOI: 10.1055/s-2007-983825
PAPER
© Georg Thieme Verlag Stuttgart · New YorkReluctant Cross-Metathesis Reactions: The Highly Beneficial Effect of Microwave Irradiation
Weitere Informationen
            
               
                  
                        
                              Received
                              20 April 2007 
                      
Publikationsdatum:
29. August 2007 (online)
            
         
      
   Publikationsverlauf
Publikationsdatum:
29. August 2007 (online)
Abstract
The beneficial effect of microwave irradiation versus classical thermal conditions is demonstrated through a series of comparative cross-metathesis reactions.
Key words
carbene complexes - catalysis - cross coupling - metathesis - olefination
- For reviews on CM, see:
 - 1a 
             
            
Vernall AJ.Abell AD. Aldrichimica Acta 2003, 36: 93 - 1b 
             
            
Connon SJ.Blechert S. Angew. Chem. Int. Ed. 2003, 42: 1900 - 1c 
             
            
Blackwell HE.O’Leary DJ.Chatterjee AK.Washenfelder RA.Bussmann DA.Grubbs RH. J. Am. Chem. Soc. 2000, 122: 58 - For a general model for selectivity in alkene CM, see:
 - 1d 
             
            
Chatterjee AK.Choi T.-L.Sanders DP.Grubbs RH. J. Am. Chem. Soc. 2003, 125: 11360 - 2 
             
            
Vedrenne E.Dupont H.Oualef S.Elkaïm L.Grimaud L. Synlett 2005, 670 - 3a 
             
            
Randl S.Gessler S.Wakamatsu H.Blechert S. Synlett 2001, 430 - 3b 
             
            
Love JA.Morgan JP.Trnka TM.Grubbs RH. Angew. Chem. Int. Ed. 2002, 41: 4035 - 3c 
             
            
Rivard M.Blechert S. Eur. J. Org. Chem. 2003, 2225 - 3d 
             
            
Michrowska A.Bujok R.Harutyunyan S.Sashuk V.Dolgonos G.Grela K. J. Am. Chem. Soc. 2004, 126: 9318 - 3e 
             
            
Bujok R.Bieniek M.Masnyk M.Michrowska A.Sarosiek A.Stepowska H.Arlt D.Grela K. J. Org. Chem. 2004, 69: 6894 - 3f 
             
            
Hoveyda HR.Vézina M. Org. Lett. 2005, 7: 2113 - 3g 
             
            
Bai C.-X.Zhang W.-Z.He R.Lu X.-B.Zhang Z.-Q. Tetrahedron Lett. 2005, 46: 7225 - 3h 
             
            
Bai C.-X.Lu X.-B.He R.Zhang W.-Z.Feng X.-J. Org. Biomol. Chem. 2005, 3: 4139 - For CM of acrylonitrile with a molybdenum-based catalyst, see:
 - 3i 
             
            
Crowe WE.Goldberg DR. J. Am. Chem. Soc. 1995, 117: 5162 - For reviews on microwave-assisted synthesis, see:
 - 4a 
             
            
Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250 - 4b 
             
            
Hayes BL. Aldrichimica Acta 2004, 37: 66 - 4c 
             
            
de la Hoz A.Díaz-Ortiz A.Moreno A. Chem. Soc. Rev. 2005, 34: 164 - For microwave-assisted RCM, see:
 - 4d 
             
            
Varray S.Gauzy C.Lamaty F.Lazaro R.Martinez J. J. Org. Chem. 2000, 65: 6787 - 4e 
             
            
Mayo KG.Nearhoof EH.Kiddle JJ. Org. Lett. 2002, 4: 1567 - 4f 
             
            
Garbacia S.Desai B.Lavastre O.Kappe CO. J. Org. Chem. 2003, 68: 9136 - 4g 
             
            
Thanh GV.Loupy A. Tetrahedron Lett. 2003, 44: 9091 - 4h 
             
            
Grigg R.Martin W.Morris J.Sridharan V. Tetrahedron Lett. 2003, 44: 4899 - 4i 
             
            
Balan D.Adolfsson H. Tetrahedron Lett. 2004, 45: 3089 - 4j 
             
            
Comer E.Organ MG. J. Am. Chem. Soc. 2005, 127: 8160 - 4k 
             
            
Nosse B.Schall A.Jeong WB.Reiser O. Adv. Synth. Catal. 2005, 347: 1869 - 4l 
             
            
Appukkuttan P.Dehaen W.Van der Eycken E. Org. Lett. 2005, 7: 2723 - 4m 
             
            
Collins SK.Grandbois A.Vachon MP.Côté J. Angew. Chem. Int. Ed. 2006, 45: 2923 - 4n 
             
            
Yang QY.Li X.-Y.Wu H.Xiao W.-J. Tetrahedron Lett. 2006, 47: 3893 - 4o 
             
            
Chapman RN.Arora PS. Org. Lett. 2006, 8: 5825 - For microwave-assisted CM, see:
 - 4p 
             
            
Poulsen S.-A.Bornaghi LF. Tetrahedron Lett. 2005, 46: 7389 - 4q 
             
            
Bargiggia FC.Murray WV. J. Org. Chem. 2005, 70: 9636 - 4r 
             
            
Morris T.Sandham D.Caddick S. Org. Biomol. Chem. 2007, 5: 1025 - 4s 
             
            
Salim SS.Bellingham RK.Brown RCD. Eur. J. Org. Chem. 2004, 800 - 4t 
             
            
Colombeau L.Zerrouki R.Krausz P.Champavier Y. Lett. Org. Chem. 2005, 2: 613 - 5 
             
            
Hong SH.Sanders DP.Lee CW.Grubbs RH. J. Am. Chem. Soc. 2005, 127: 17160 - 6 As CM is a reversible process, the TON (turnover number) represents the average number of substrate molecules converted into the cross product per molecule of catalyst.
            A typical loading of 1a,b in CM reaction is  2-10%, which corresponds to a maximum TON of 10-50. For a recent
            TON study in ruthenium carbene catalyzed ring-closing metathesis, see:  
            
Maechling S.Zaja M.Blechert S. Adv. Synth. Catal. 2005, 347: 1413