Journal Pre-proof
Later, gramscale reaction and the catalyst recoverystudies were performed underoptimised conditions. Thus,phenyl acetylene and
o
isatin were reacted in presence ofthe catalyst andDABCOin water(60 C, 3h) to the desired product in 90% yield (for procedure, see
electronic supporting information). Similarly, the catalyst (CuWO4 nanoparticles) was recovered fromthe reaction mixture by simple
filtration, washed with ethylacetateand acetone (3X 5 mL), heated at 80 oC in the oven foractivation andreused forthe reaction up to
6 cycles withoutlosing activity giving the desired product (Table 1 of electronic supporting information). The powder XRD data of
recycled catalyst indicating that there is no change in the morphology of the catalyst even after 6th cycle of the reaction [overlapping
image of Powder XRD of original catalyst and recovered catalyst after 6th cycle is given in electronic supporting information).
4. Conclusions
In conclusion,we have developeda simple and efficient method forthe synthesisof3-hydroxy-3-(arylethynyl)indolin-2-ones via C-
H activation of arylacetylenes and 3-hydroxy-3-(1H-indol-3-yl)indolin-2-ones, bis-indolyl indoles via Friedel-Crafts alkylation of
isatins usingCuWO4 nanoparticles as recyclable heterogeneouscatalyst in aqueousmedium.All three types of reactions gave good to
excellent yields.This is the first example where CuWO4 nanoparticleshave beenused forthe C-H activation of phenyl acetylenes and
Friedel-Crafts alkylation of indoles with isatins.
Acknowledgements
BP thanks MHRD for fellowship. KS thanks DST for the INSPIRE fellowship. SN thanks, UGC-New Delhi for the fellowship. DK
thanks, DST (SERB), New Delhi for the financial support (SB/FT/CS-136/2012 and SB/EMEQ-103/2014).
Declaration of interests: None
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Graphical abstract:
Highlights:
Direct spC-H activation of phenyl acetylenes in aqueous medium
First application of CuWO4 nanoparticles for organic transformation
CuWO4 nanoparticles as recyclable heterogeneous catalyst
Selective synthesis of 3-hydroxy-3-(indol-3-yl) indolin-2-one at room temperature