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Sharpless epoxidation & suzuki coupling

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Useful content for postgraduates students of Pharmaceutical and Medicinal Chemistry and undergraduate students of Organic Chemistry

Useful content for postgraduates students of Pharmaceutical and Medicinal Chemistry and undergraduate students of Organic Chemistry

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  • 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
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  • 18. SUZUKI COUPLING INTRODUCTION
  • 19. REACTION :
  • 20. MECHANISM :
  • 21. MECHANISM :
  • 22. OTHER CATALYST USED :
    • NICKEL ON CHARCOAL
    • RHODIUM CATALYST
    • SILVER OXIDE MEDIATED PALLADIUM CATALYST
    • TRI-TERT BUTYL PHOSPHINE
  • 23. ADVANTAGES :
    • Mild reaction conditions
    • Availability of boronic acids
    • Boronic acids –less toxic
    • stereo selectivity
    • Removal of byproducts
  • 24. DISADVANTAGES :
    • Reaction of aryl halides
    • Self coupling products
    • Formation of phosphine bound aryls
    • Racemisation of optically active compound
    • Aldol condensation
  • 25. APPLICATION :
  • 26.
    • Recent Literature
    • 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.
    • 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.
    • Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids I. Kondolff, H. Doucet, M. Santelli, Tetrahedron, 2004 , 60 , 3813-3818.
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    • 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.
    • 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.
    • 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
  • 28. IMPROVEMENTS :
    • Development of catalyst facilitating coupling of unreactive aryl halides
    • Use of aryl, alkyl trifluroboronates in place of boronic acids