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Chemodivergent Couplings of N-Arylureas and Methyleneoxetanones via Rh(III)-Catalyzed and Solvent-Controlled C-H Activation.

Guoxun ZhuWendi ShiHui GaoZhi ZhouHuacan SongWei Yi
Published in: Organic letters (2019)
The efficient couplings of diverse N-arylureas and methyleneoxetanones have been realized via Rh(III)-catalyzed and solvent-controlled chemoselective C-H functionalization, which involved the tunable β-H elimination and β-O elimination processes, thereby giving divergent access to quinolin-2(1 H)-ones and ortho-allylated N-arylureas with broad substrate compatibility and good functional group tolerance. the divergent synthetic utilities of the transformations have also been exemplified by subsequently tandem C-H allylation, unsymmetrical C-H functionalization, alternative reaction mode, as well as removal of the carbamoyl group.
Keyphrases
  • room temperature
  • ionic liquid