期刊
TETRAHEDRON
卷 72, 期 8, 页码 1095-1104出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.01.005
关键词
Geminal diamination; Geminal aminooxygenation; Hypervalent iodine; Metal-free conditions; Semi-pinacol rearrangement
资金
- CSIR-India
- JNCASR
- DST, India
- IIsc
We report here the first general method for the geminal diamination and an intermolecular metal-free, geminal aminooxygenation of vinylarenes using hypervalent iodine reagent. A new m-CPBA mediated geminal aminooxygenation is also reported. A novel reagent-switch for the control of migrating group by controlling the two independent geminal addition paths is developed. Deuterium labelling studies and the control studies have provided unambiguous evidences for the phenyl migration and hydride migration in the oxidative geminal difunctionalization process mediated by Phl(OCOCF3)(2) and m-CPBA, respectively through a semi-pinacol rearrangement. (C) 2016 Elsevier Ltd. All rights reserved.
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