4.8 Article

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

Journal

ORGANIC LETTERS
Volume 21, Issue 11, Pages 4143-4147

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01333

Keywords

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Funding

  1. NSFC [21877020]
  2. Guangdong Natural Science Funds for Distinguished Young Scholar [2017A030306031]
  3. Natural Science Foundation of Guangdong Province [2018A030313274]

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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 beta-H elimination and beta-O elimination processes, thereby giving divergent access to quinolin-2(1H)-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.

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