Journal
CHEMICAL SCIENCE
Volume 5, Issue 6, Pages 2416-2421Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4sc00652f
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Funding
- AstraZeneca
- University of Bristol
- EPSRC [EP/G036764/1, EP/J007455/1]
- EPSRC [EP/K03927X/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/J007455/1, 981192, EP/K03927X/1, 1100702] Funding Source: researchfish
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Copper catalyzed Heck-like cyclizations of oxime esters are described. Mechanistic studies indicate a reaction pathway that proceeds via the generation and cyclization of an intermediate that possesses iminyl radical character. To the best of our knowledge, this work encompasses the first examples of Cu-catalyzed aza-Heck reactions that proceed via oxidative initiation at nitrogen to generate products containing a new alkene. This new protocol is also an effective alternative to Pd-based systems and highlights the value of replacing precious metal catalysts with cheaper and more sustainable variants.
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