Aminooxygenation of Ynamides with N-Hydroxybenzotriazoles: Synthesis of alpha-Benzotriazolyl Carbonyl Compounds
- Title
- Aminooxygenation of Ynamides with N-Hydroxybenzotriazoles: Synthesis of alpha-Benzotriazolyl Carbonyl Compounds
- Author
- 조천규
- Keywords
- GOLD-CATALYZED ADDITION; ALKYNES; CARBENE; REARRANGEMENT; DISCOVERY; ACCESS
- Issue Date
- 2020-04
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v. 85, no. 11, page. 6935-6950
- Abstract
- Addition of N-hydroxybenzotriazoles to ynamides causes spontaneous rearrangement, resulting in alpha-benzotriazolyl imides. The transformation proceeded at rt in the absence of any catalyst but could be efficiently catalyzed by Zn(OTf)(2). Crossover experiments confirmed that the rearrangement is an intramolecular process, most likely via a concerted mechanism. However, heating the mixture above 110 degrees C resulted in isomerization of N2 into N1 product, via heterolytic C-N bond dissociation. This tandem addition-rearrangement sequence provides an efficient and atom-economical synthetic route for the synthesis of alpha-benzotriazolyl carbonyl compounds.
- URI
- https://pubs.acs.org/doi/10.1021/acs.joc.0c00174https://repository.hanyang.ac.kr/handle/20.500.11754/165736
- ISSN
- 0022-3263; 1520-6904
- DOI
- 10.1021/acs.joc.0c00174
- Appears in Collections:
- COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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