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Download fileSustainable Palladium-Catalyzed Tsuji–Trost Reactions Enabled by Aqueous Micellar Catalysis
journal contribution
posted on 18.06.2020, 13:06 authored by Nicholas
R. Lee, Farbod A. Moghadam, Felipe C. Braga, Daniel J. Lippincott, Bingchun Zhu, Fabrice Gallou, Bruce H. LipshutzPalladium-catalyzed
allylic substitution, or “Tsuji–Trost”
reactions, can be run under micellar catalysis conditions featuring
not only chemistry in water but also numerous combinations of reaction
partners that require low levels of palladium, typically on the order
of 1000 ppm (0.1 mol %). These couplings are further characterized
by especially mild conditions, leading to a number of cases not previously
reported in an aqueous micellar medium. Inclusion of diverse nucleophiles,
such as N–H heterocycles, alcohols, dicarbonyl compounds, and
sulfonamides is described. Intramolecular cyclizations further illustrate
the broad utility of this process. In addition to recycling studies,
a multigram scale example is reported, indicative of the prospects
for scale up.
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prospectdicarbonyl compoundsrecycling studiesTsujiAqueous Micellar Catalysis Palladium-catalyzed allylic substitutionppmmicellar catalysis conditionsPalladium-Catalyzedutilitymicellar mediumheterocyclemultigram scale examplereaction partnerscombinationIntramolecular cyclizationsEnabledsulfonamideSustainablepalladiumnucleophilecouplingInclusion