Cyclization Reaction for the Synthesis of Polysubstituted Naphthalenes in the Presence of Au(I) Precatalysts
- Authors
- Jagdale, Arun R.; Park, Jong Hyub; Youn, So Won
- Issue Date
- Sep-2011
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.76, no.17, pp.7204 - 7215
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 76
- Number
- 17
- Start Page
- 7204
- End Page
- 7215
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/144846
- DOI
- 10.1021/jo201339z
- ISSN
- 0022-3263
- Abstract
- Au(I)-catalyzed cyclization of alkenyl carbonyl compounds leading to a variety of substituted naphthalenes has been developed. This process exploits a dual function of the Au(I) catalyst: (1) the oxophilic nature of the Au(I) catalyst, counterintuitive to the pi-acidic reactivities generally associated with Au catalysts, and (2) olefin isomerization supported by the outcome of isotope scrambling experiments. It cannot be completely excluded that TfOH is a true operative catalyst in this protocol. In view of the practicality, the unnecessity of isomerically pure starting material in this reaction is particularly attractive and valuable.
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