Journal
ORGANIC LETTERS
Volume 23, Issue 15, Pages 6169-6173Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02359
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Funding
- Research Grants Council of Hong Kong [CUHK 14301820]
- Chinese University of Hong Kong (Faculty of Science Direct Grant for Research)
- Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
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In this study, a nucleophilic vinylic substitution reaction was developed to efficiently synthesize trisubstituted alkenes with stereocontrol under simple conditions. Additionally, dimerization of monofluoroalkenes to form (E,E)-divinyl ethers was observed, triggered by adventitious water in the reaction mixture.
We herein describe a nucleophilic vinylic substitution (SNV) of trisubstituted monofluoroalkenes with excellent stereocontrol (d.r. > 99:1). Starting from (E)-beta-monofluoroacrylates, various trisubstituted (E)-alkenes containing O/N/S-substituent groups at the vinylic position can be obtained under simple conditions. Furthermore, (E,E)-divinyl ethers can be generated through dimerization of the monofluoroalkenes, triggered by adventitious water in the reaction mixture.
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