4.4 Article

Photoswitchable organocatalysis in acylation of alcohol using dithienylethene-linked azoles

Journal

TETRAHEDRON
Volume 69, Issue 52, Pages 11064-11069

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.11.015

Keywords

Photoswitch; Organocatalysis; Azoles; Dithienylethenes; Acylation

Funding

  1. Japan Society for the Promotion of Science (JSPS)
  2. Grants-in-Aid for Scientific Research [23750123] Funding Source: KAKEN

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Three novel dithienylethenes bearing azole derivatives were synthesized and found to undergo reversible photocyclization of the dithienylethene units upon alternate irradiation with UV and visible light. Among them, the dithienylethene-linked imidazole and N-phenylimidazole exhibited a relatively high organocatalytic activity for the acylation of 2-decanol with acetic anhydride, and the catalytic activity of the dithienylethene-linked imidazole could be switched by reversible photoinduced cyclization/cycloreversion of the dithienylethene unit. (C) 2013 Elsevier Ltd. All rights reserved.

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