SHARPLESS EPOXIDATION & SUZUKI COUPLING Dr. Amit G.Nerkar, Associate Professor, Post Graduate Dept. of Pharmaceutical Chem...
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
SUZUKI COUPLING  INTRODUCTION
REACTION :
MECHANISM :
MECHANISM :
OTHER CATALYST USED : <ul><li>NICKEL ON CHARCOAL </li></ul><ul><li>RHODIUM CATALYST </li></ul><ul><li>SILVER OXIDE MEDIATE...
ADVANTAGES : <ul><li>Mild reaction conditions </li></ul><ul><li>Availability of boronic acids </li></ul><ul><li>Boronic ac...
DISADVANTAGES : <ul><li>Reaction of aryl halides </li></ul><ul><li>Self coupling products </li></ul><ul><li>Formation of p...
APPLICATION :
<ul><li>Recent Literature </li></ul><ul><li>Alkyl-Alkyl Suzuki Cross-Couplings of Unactivated Secondary Alkyl Halides at R...
<ul><li>Pd( N,N -Dimethyl β-alaninate)2 as a High-Turnover-Number, Phosphine-Free Catalyst for the Suzuki Reaction X. Cui,...
IMPROVEMENTS : <ul><li>Development of catalyst facilitating coupling of unreactive  aryl halides </li></ul><ul><li>Use of ...
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Sharpless epoxidation & suzuki coupling

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Sharpless epoxidation & suzuki coupling

  1. 1. SHARPLESS EPOXIDATION & SUZUKI COUPLING Dr. Amit G.Nerkar, Associate Professor, Post Graduate Dept. of Pharmaceutical Chemistry, Smt.Kashibai Navale College of Pharmacy, Kondhwa (Bk), Pune-48
  2. 18. SUZUKI COUPLING INTRODUCTION
  3. 19. REACTION :
  4. 20. MECHANISM :
  5. 21. MECHANISM :
  6. 22. OTHER CATALYST USED : <ul><li>NICKEL ON CHARCOAL </li></ul><ul><li>RHODIUM CATALYST </li></ul><ul><li>SILVER OXIDE MEDIATED PALLADIUM CATALYST </li></ul><ul><li>TRI-TERT BUTYL PHOSPHINE </li></ul>
  7. 23. ADVANTAGES : <ul><li>Mild reaction conditions </li></ul><ul><li>Availability of boronic acids </li></ul><ul><li>Boronic acids –less toxic </li></ul><ul><li>stereo selectivity </li></ul><ul><li>Removal of byproducts </li></ul>
  8. 24. DISADVANTAGES : <ul><li>Reaction of aryl halides </li></ul><ul><li>Self coupling products </li></ul><ul><li>Formation of phosphine bound aryls </li></ul><ul><li>Racemisation of optically active compound </li></ul><ul><li>Aldol condensation </li></ul>
  9. 25. APPLICATION :
  10. 26. <ul><li>Recent Literature </li></ul><ul><li>Alkyl-Alkyl Suzuki Cross-Couplings of Unactivated Secondary Alkyl Halides at Room Temperature B. Saito, G. C. Fu, J. Am. Chem. Soc. , 2007 , 129 , 9602-9603. </li></ul><ul><li>Boronic Acids: New Coupling Partners in Room-Temperature Suzuki Reactions of Alkyl Bromides. Crystallographic Characterization of an Oxidative-Addition Adduct Generated under Remarkably Mild Conditions J. H. Kirchhoff, M. R. Netherton, I. D. Hill, G. C. Fu, J. Am. Chem. Soc. , 2002 , 124 , 13662-13663. </li></ul><ul><li>Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids I. Kondolff, H. Doucet, M. Santelli, Tetrahedron, 2004 , 60 , 3813-3818. </li></ul>
  11. 27. <ul><li>Pd( N,N -Dimethyl β-alaninate)2 as a High-Turnover-Number, Phosphine-Free Catalyst for the Suzuki Reaction X. Cui, T. Qin, J.-R. Wang, L. Liu, Q.-X. Guo, Synthesis , 2007 , 393-399. </li></ul><ul><li>Guanidine/Pd(OAc)2-Catalyzed Room Temperature Suzuki Cross-Coupling Reaction in Aqueous Media under Aerobic Conditions S. Li, Y. Lin, J. Cao, S. Zhang, J. Org. Chem. , 2007 , 72 , 4067-4072. </li></ul><ul><li>Biphenylene-Substituted Ruthenocenylphosphine for Suzuki-Miyaura Coupling of Aryl Chlorides T. Hoshi, T. Nakazawa, I. Saitoh, Y. Mori, T. Suzuki, J.-i. Sakai, H. Hagiwara, S. Akai, Org. Lett. , 2008 , 10 , 2063-2066 </li></ul>
  12. 28. IMPROVEMENTS : <ul><li>Development of catalyst facilitating coupling of unreactive aryl halides </li></ul><ul><li>Use of aryl, alkyl trifluroboronates in place of boronic acids </li></ul>

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