4.7 Article

Oxidant controlled regioselective mono- and di-functionalization reactions of coumarins

Journal

CHEMICAL COMMUNICATIONS
Volume 51, Issue 84, Pages 15422-15425

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5cc06200d

Keywords

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Funding

  1. Department of Science and Technology (DST), New Delhi [SB/S1/OC-53/2013]
  2. Council of Scientific and Industrial Research (CSIR) [02(0096)/12/EMR-II]
  3. MHRD [5-5/2014-TS-VII]

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C-3 alkylation of coumarins has been accomplished using cycloalkanes or alkylbenzenes in the presence of di-tert-butylperoxide (DTBP) and Fe-III catalyst. Under metal free conditions and just by switching the oxidant from DTBP to TBHP, an exclusive C-4 cycloalkylation-C-3 peroxidation reaction takes place. During C-3 alkylation, the C-C bond formation occurs at the expense of an existing C-C bond, while the C-4 alkylation is associated with the formation of new C-C and C-O bonds.

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