期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 17, 页码 7307-7312出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo3009963
关键词
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资金
- National Research Foundation of Korea (NRF)
- Ministry of Education, Science and Technology [2012001725, 2011K000675, 2012008875]
- National Research Foundation of Korea [2010-50247, 2012R1A1B3001725, 2010-50244, 2012R1A2A2A02008875] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
A simple catalytic system that uses commercially available cobalt(II) perchlorate as the catalyst and 3-chloroperoxybenzoic acid as the oxidant was found to be very effective in the epoxidation of a variety of olefins with high product selectivity under mild experimental conditions. More challenging targets such as terminal aliphatic olefins were also efficiently and selectively oxidized to the corresponding epoxides. This catalytic system features a nearly nonradical-type and highly stereospecific epoxidation of aliphatic olefin, fast conversion, and high yields. Olefin epoxidation by this catalytic system is proposed to involve a new reactive Co-II-OOC(O)R species, based on evidence from (H2O)-O-18-exchange experiments, the use of peroxyphenylacetic acid as a mechanistic probe, reactivity and Hammett studies, EPR, and ESI-mass spectrometric investigation. However, the O-O bond of a Co-II-acylperoxo intermediate (Co-II-OOC(O)R) was found to be cleaved both heterolytically and homolytically if there is no substrate.
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