Synlett 2017; 28(12): 1481-1485
DOI: 10.1055/s-0036-1588990
© Georg Thieme Verlag Stuttgart · New York

Metal-Free Oxidative C=C Bond Cleavage of Electron-Deficient Enamines Promoted by tert-Butyl Hydroperoxide

Mehdi Adib*a, Rahim Pashazadeha, Seyed Jamal Adin Goharib, Fatemeh Shahsavaric
  • aSchool of Chemistry, College of Science, University of Tehran, P. O. Box 14155-6455, Tehran, Iran   Email:
  • bDepartment of Chemistry, Imam Hossein University, Tehran, Iran
  • cNational Petrochemical Company, Petrochemical Research and Technology Company, Tehran, Iran
Further Information

Publication History

Received: 29 November 2016

Accepted after revision: 08 March 2017

Publication Date:
19 April 2017 (eFirst)


A novel tert-butyl hydroperoxide (TBHP)-promoted oxidative C=C double-bond cleavage of enamines is described. Heating a solution of an electron-deficient enamine in chlorobenzene at 80 °C in the presence of TBHP for two hours led to cleavage of the C=C bond. This study offers a new strategy to carry out C=O double-bond formation by the use of TBHP.

Supporting Information