4.8 Article

Photochemical Hydroacylation of Michael Acceptors Utilizing an Aldehyde as Photoinitiator

Journal

CHEMSUSCHEM
Volume 12, Issue 18, Pages 4194-4201

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201901725

Keywords

4-cyanobenzaldehyde; hydroacylation; Michael acceptors; photochemistry; photoinitiator

Funding

  1. John Latsis Foundation
  2. Laboratory of Organic Chemistry of the Department of Chemistry of the National and Kapodistrian University of Athens
  3. State Scholarship Foundation (IKY)
  4. COST Action C-H Activation in Organic Synthesis (CHAOS) [CA15106]

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The hydroacylation of Michael acceptors constitutes a useful tool for the formation of new C-C bonds. In this work, an environmentally friendly procedure was developed, utilizing 4cyanobenzaldehyde as the photoinitiator and household bulbs as the irradiation source. A great variety of substrates was well-tolerated, leading to good yields, and mechanistic experiments were performed to elucidate the catalyst's possible mechanistic pathway. Moreover, the inherent selectivity challenge regarding alpha,alpha-disubstituted aldehydes (decarbonylation problem) was studied and addressed.

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