Journal
ACS CATALYSIS
Volume 7, Issue 12, Pages 8441-8445Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03432
Keywords
aminoarylation; nickel catalysis; oximes; pyrrolines; radicals
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Funding
- Swedish Research Council, VR [621-2012-2981]
- Carl Trygger foundation
- Wenner-Gren Foundations
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A nickel-catalyzed 1,2-aminoarylation of oximeester-tethered alkenes with boronic acids was developed. A variety of pyrroline derivatives were synthesized in good yields via the successive formation of C(sp(3))-N and C(sp(3))-C(sp(2)) bonds. For cyclobutanone-derived oxime esters, the reaction provided aliphatic nitriles incorporating an aromatic group in the gamma-position. A mechanism involving iminyl radical and carbon-centered radical intermediates was proposed.
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