4.7 Article

Visible-Light Driven Photocascade Catalysis: Union of N,N-Dimethylanilines and α-Azidochalcones in Flow Microreactors

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 4, Pages 2249-2256

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02932

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Funding

  1. Science and Engineering Research Board, Department of Science AMP
  2. Technology, Ministry of Science and Technology India [GAP-0744, GPP-0313]
  3. University Grants Commission, New Delhi
  4. National Institute of Pharmaceutical Education and Research, Hyderabad

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N,N-Dimethylanilines were coupled with aazidochalcones using visible-light driven Ru(bpy)(3)(PF6)(2) catalyzed photocascade continuous flow microfluidic approach that involves the creation of one C-C and two C-N new bonds. The reaction involves dual photocatalysis ensuing two sp(3) C-H bond functionalization of N,N-dimethylanilines. To explore the scope of the reaction, 20 different 1,3-diazabicyclo[3.1.0]hexanes were synthesized in good yields (55-71%).

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