Multi-step reaction with 7 steps
1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 18 h / 20 °C / Inert atmosphere
2: N-Bromosuccinimide; silver fluoride / acetonitrile / 18 h / 20 °C / Darkness
3: lithium chloride; bis(η3-allyl-μ-chloropalladium(II)); 1,5-cis,cis-cyclooctadiene; acetic acid / 18 h / 80 °C
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 6 h / 20 °C
5: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / tetrahydrofuran; water / 6 h / 50 °C / Darkness
6: (2-bromophenyl)boronic acid / 1,2-dichloro-ethane / 18 h / Reflux
7: tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl / tert-butyl alcohol / 72 h / 110 °C / Molecular sieve; Inert atmosphere
With
2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); N-Bromosuccinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 1,5-cis,cis-cyclooctadiene; bis(η3-allyl-μ-chloropalladium(II)); lithium hydroxide monohydrate; silver fluoride; caesium carbonate; acetic acid; triethylamine; lithium chloride; (2-bromophenyl)boronic acid;
In
tetrahydrofuran; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol;
1: |Sonogashira Cross-Coupling / 6: |Diels-Alder Cycloaddition / 7: |Buchwald-Hartwig Coupling;
DOI:10.1039/c4cc01830c