Visible-light-induced cyanation of aza-Baylis–Hillman adducts: a Michael type addition

Visible-light-induced cyanation of aza-Baylis–Hillman adducts: a Michael type addition

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 4π conjugated iminium ion intermediates, which undergo cyanation at the γ-position t...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 55; no. 10; pp. 1788 - 1792
Main Authors: Srivastava, Vishnu P., Yadav, Arvind K., Yadav, Lal Dhar S.
Format: Journal Article
Language:English
Published: Elsevier Ltd 05-03-2014
Subjects:
Adducts
Air oxidation
Baylis–Hillman adducts
Catalysis
Cyanation
Cyanides
Economics
Formations
Michael adducts
Oxidants
Oxidizing agents
Photoredox catalysis
Tetrahedrons
Visible light
Photoredox catalysis
Michael adducts
Visible light
Baylis–Hillman adducts
Air oxidation
Cyanation
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Summary: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 4π conjugated iminium ion intermediates, which undergo cyanation at the γ-position to afford Michael type adducts. This is the first example of visible-light-induced catalytic functionalization of aza-BH adducts using air (O2) as an economical and ecosustainable oxidant and TMSCN as a convenient and readily available cyanide source.
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ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.01.121