4.5 Article

Diastereoselective sp3-C-H Functionalization of Arylmethyl Ketones and Transformation of E- to Z-Products Through Photocatalysis

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 4, Pages 424-428

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901415

Keywords

Arylmethylketones; C-H functionalization; Diastereoselectivity; 1; 4-Enediones; Photocatalysis

Funding

  1. Science and Engineering Research Board (SERB), India [SB/FT/CS-073/2014]
  2. MHRD, Govt of India under the TEQIP-III Project

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We have developed an efficient metal-free route for the synthesis of 1,4-enedione derivatives under microwave irradiation by reacting easily available arylmethylketones with DMSO or diphenyl sulfoxide in the presence of TBAI and persulfate. The reaction is very clean and completes within very short time. All the reagents and catalysts are cheap and environmentally benign. In addition, the E-isomer of the products can easily be transformed into the Z-isomer by using eosin Y photocatalyst under the irradiation of white CFL.

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