Journal of Jishou University(Natural Sciences Edition)

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Cu/Fe Co-Catalyzed Cascade Addition/Cyclization of Alkenes Toward Isoquinolinediones

XIA Lülu,WANG Liangneng,LI Zengzeng,SHENG Huixiang,TANG Shi   

  1. (National Demonstration Center for Experimental Chemistry Education,Jishou University,Jishou 416000,Hunan China)
  • Online:2018-11-25 Published:2018-12-07


A Cu/Fe-cocatalyzed cascade addition/cyclizaion/cross-coupling of N-methacryloyl halobenzamides with azo reagents toward dual tert-alkylating isoquinolinediones was developed.Under the synergistic CuI/Fe catalysis,alkyl azo reagent mediated a cascade addition/cyclization of N-alkyl-N-methacryloyl halobenzamides,followed by further radical cross-coupling via the cleavage of C—Cl bond with site selectivity,leading to a series of dual tert-alkylating isoquinolinediones in 41%~78% yields.The reaction realized the radical cross-coupling of azo reagent with hyper-conjugated free radicals arising from a prior dearomatzation of methacryloyl halobenzamides and constructed the carbon (tertiary) -carbon bond at the position of C—Cl bond,thereby providing a new idea exploring the tertiary alkyl-aryl cross-coupling reactions.

Key words: isoquinolinediones, radical cross-coupling, synergistic Cu/Fe catalysis, alkyl azo reagent, tandem reaction

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