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- Title
Metal-Free Synthesis of 3-Arylquinolin-2-ones from N,2-Diaryl- acrylamides via Phenyliodine(III) Bis(2,2-dimethylpropanoate)- Mediated Direct Oxidative C−C Bond Formation.
- Authors
Cao, Yang; Zhao, Hui; Zhang ‐ Negrerie, Daisy; Du, Yunfei; Zhao, Kang
- Abstract
Treatment of N,2-diarylacrylamides with the organoiodine(III) compound phenyliodine(III) bis(2,2-dimethylpropanoate) [PhI(O2C- t-Bu)2] and boron trifluoride etherate (BF3⋅Et2O) resulted in a direct and selective oxidative C( sp2)−C( sp2) bond formation leading to a convenient assemblage, under mild conditions, of the biologically important 3-arylquinolin-2-one skeleton. Differing from the five-membered oxindole products from oxidative cyclizations mediated by transition metals, this metal-free approach realized a direct annulation of the N-arylacrylamide into a six-membered 3-arylquinolin-2-one skeleton.
- Subjects
ORGANOIODINE compounds; BOND formation mechanism; CHEMICAL bonds; ANNULATION; TRANSITION metal compounds
- Publication
Advanced Synthesis & Catalysis, 2016, Vol 358, Issue 22, p3610
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201600512