Gold-catalysed oxyarylation of styrenes and mono- and gem-disubstituted olefins facilitated by an iodine(III) oxidant.
1-Hydroxy-1,2-benziodoxol-3(1H)-one (IBA) is an efficient terminal oxidant for gold-catalysed, three-component oxyarylation reactions. The use of this iodine(III) reagent expands the scope of oxyarylation to include styrenes and gem-disubstituted olefins, substrates that are incompatible with the previously reported Selectfluor-based methodology. Diverse arylsilane coupling partners can be employed, and in benzotrifluoride, homocoupling is substantially reduced. In addition, the IBA-derived co-products can be recovered and recycled.
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS UK.
Liam T
LT
Ball
Guy C
GC
Lloyd-Jones
Christopher A
CA
Russell
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry*; D013343:Styrenes / Q000737:chemistry*
D000475:Alkenes; D016877:Oxidants; D013343:Styrenes; D006046:Gold; D007455:Iodine