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Palladium Catalysis Townsend Group Meeting Dorothy Ackerman August 4, 2015.

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Presentation on theme: "Palladium Catalysis Townsend Group Meeting Dorothy Ackerman August 4, 2015."— Presentation transcript:

1 Palladium Catalysis Townsend Group Meeting Dorothy Ackerman August 4, 2015

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3 Timeline of metal-catalyzed cross- coupling reactions T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

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5 Characteristics of Pd-Catalyzed Reactions Versatile Tolerant Robust Low toxicity T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

6 Catalytic Cycles Acros Brochure, “Palladium-Catalysed Coupling Chemistry.”

7 Origins of Cross-Coupling Reactions T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

8 Origins of Cross-Coupling Reactions T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

9 Origins of Cross-Coupling Reactions Set of standard requirements for coupling processes: 1)An organohalide as a coupling partner 2)A stoichiomentric organometallic partner 3)A transition metal to effect the C-C bond forming event T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

10 History of Palladium Discovered by Wollaston in 1802 Percival Norton Johnson advertized several uses for palladium T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

11 Palladium finally gets its day in the sun “The initial Wacker Chemie research would serve as the inspiration for one of the most important discoveries in organic synthesis during the 20 th century.” Walter Hafner T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

12 Palladium gets its start in cross- coupling: Heck Reaction T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

13 Palladium gets its start in cross- coupling T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

14 Sonogashira Reaction T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

15 Corriu-Kumada Reaction T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

16 Negishi Reaction T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

17 Negishi Reaction T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

18 Stille Coupling T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

19 Suzuki-Miyaura Coupling T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

20 Miyaura Borylation T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

21 Hiyama T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085. Org. Lett., 2000, 2, 2491

22 Buchwald-Hartwig T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

23 Tsuji-Trost Allylation T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

24 Tsuji-Trost Allylation Hard nucleophiles: Soft nucleophiles: B. Trost, D. Van Vranken Chem. Rev., 1996, 96, 395-422

25 α-Arylation T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

26 Decarboxylative Coupling T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

27 C-H Activation T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085. J. Yamaguchi, A. D. Yamaguchi, K. Itami ACIE, 2012, 51, 8960-9009.

28 Improvements of Ligands P(t-Bu) 2 MePd(OAc) 2 T. J. Colacot, V. Snieckus, et al. ACIE, 2012, 51, 5062-5085.

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33 P. Baumeister, G. Seifert, H. Steiner, European Patent EP584043, 1994 A. K. Schrock, U.S. Patent US4812588, 1989. B. A. Anderson, L. M. Becke, R. N. Booher, M. E. Flaugh, N. K. Harn, T. J. Kress, D. L. Varie, J. P. Wepsiec, J. Org. Chem. 1997, 62, 8634. K. Eicken, H. Rang, A. Harreus, N. Götz, E. Ammermann, G. Lorentz, and S. Strathmann, German Patent DE19531813, 1997. K. Eicken, M. Rack, F. Wetterich, E. Ammermann, G. Lorentz, and S. Strathmann, German Patent DE19735224, 1999. A. M. Rouhi, Chem. & Eng. News 2004, 82 (36), Sept. 6, pp 49-58. Industrial Examples

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