4.8 Article

Photochemical synthesis of acetals utilizing Schreiner's thiourea as the catalyst

Journal

GREEN CHEMISTRY
Volume 22, Issue 11, Pages 3539-3545

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0gc01135e

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Funding

  1. Hellenic Foundation for Research and Innovation (HFRI) [655, 721]
  2. State Scholarships Foundation (IKY)
  3. European Union (European Social Fund-ESF) [MIS-5000432]

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Acetalization of aldehydes is an area of great importance in Organic Chemistry for both synthetic and biological puproses. Herein, we report a mild, inexpensive and green photochemical protocol, where Schreiner's thiourea (N,N '-bis[3,5-bis(trifluoromethyl)-phenyl]-thiourea) is utilized as the catalyst and cheap household lamps as the light source. A variety of aromatic and aliphatic aldehydes were converted into acetals in good to high yields (23 examples, 36-96% yield) and an example of the synthesis of a cyclic acetal is provided. The reaction mechanism was also studied.

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