Utilization of sequential palladium-catalyzed cross-coupling reactions in the stereospecific synthesis of trisubstituted olefins

Organic Process Research and Development

Volumn 13, Issue 3, 2009, Pages 598-606

  Houpis, Ioannis N ^a   Shilds, Didier ^a   Nettekoven, Ulrike ^b   Schnyder, Anita ^b   Bappert, Erhart ^b   Weerts, Koen ^a   Canters, Martine ^a   Vermuelen, Wim ^a  

^a JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

^b SOLVIAS AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 66249114329     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900015g     Document Type: Article

References (31)

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18. Reasonable variations of the prescribed conditions were attempted, such as temperature, Pd:ligand ratio, base and catalyst loading, without significant success.
19. Use of the silyl protected acetylene in the presence of N-heterocyclic carbenes was also not successful in this transformation: Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020.
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21. Lower catalyst loads seemed to afford "cleaner" (less colored) reaction mixtures; however, reducing the pre-catalyst load below the 0.5 mol % level led to incomplete reactions.
22. SilicaBond-thiol is an efficient method for removing both Pd(II) and Pd(0) dissolved in reaction mixtures. It is marketed by Silicycle Corporation, and information and specification including efficiency of removal of Pd and other transition metal catalysts can be found at http://www.silicycle. com.
23. The initial screening experiments were conducted in autoclave-type vessels where evaporation of the components was not an issue. However, when typical "bench-top" experimental setups were used, some evaporation was observed (despite the presence of a condenser) that necessitated further addition of amine and propargyl alcohol to drive the reaction to completion.
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25. The Jamison group (ref 3b) has elegantly demonstrated a complementary strategy where the resulting aluminate species is transmetallated to a Cu reagent and then functionalized via alkylation to afford stereodefined trisubstituted olefins.
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27. Control experiments had established that this transformation proceeds in almost quantitative yield.
28. The screen consisted of combinations of the following: Solvents: NMP, THF, Dioxane, Toluene; Pd source: Pd(OAc)2, Pd2(dba)3-CHCl3; Ligands: [OMe3Ph]3P, [OMe2Ph]3P t-BuPh2P, t-Bu3P, CTQPHOS, DPEPHOS, dppf, P(o-tolyl)3, Degussa catCXium kit.
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