Journal
TETRAHEDRON LETTERS
Volume 55, Issue 10, Pages 1788-1792Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.01.121
Keywords
Air oxidation; Baylis-Hillman adducts; Cyanation; Michael adducts; Photoredox catalysis; Visible light
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Funding
- Department of Science and Technology (DST) Govt. of India [IFA-11CH-08]
- CSIR, New Delhi
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Visible-light-induced aerobic oxidative cyanation of aza-Baylis-Hillman (aza-BH) adducts providing valuable allylic cyanides in good to excellent yields has been developed. The protocol involves in situ formation of 4 pi conjugated iminium ion intermediates, which undergo cyanation at the gamma-position to afford Michael type adducts. This is the first example of visible-light-induced catalytic functionalization of aza-BH adducts using air (O-2) as an economical and ecosustainable oxidant and TMSCN as a convenient and readily available cyanide source. (C) 2014 Elsevier Ltd. All rights reserved.
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