Journal
ORGANIC LETTERS
Volume 23, Issue 13, Pages 5241-5245Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01768
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Funding
- Research Grants Council of Hong Kong [N_CUHK403/20]
- 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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A highly diastereoselective Pd(0)-catalyzed synthesis of difluorinated 1,3-dienes has been described, utilizing a stereoselective twofold Pd-catalyzed Miyaura borylation/Suzuki-Miyaura cross-coupling of the C-F bond. The modular synthesis of symmetrical and unsymmetrical difluorinated 1,3-dienes is achievable through different reaction pathways.
A highly diastereoselective Pd(0)-catalyzed synthesis of difluorinated 1,3-dienes is described. Symmetrical 1,3-dienes containing a vicinal difluoro moiety can be obtained as single diastereomers from tetrasubstituted gem-difluoroalkenes. The reaction presumably proceeds through a stereoselective twofold Pd-catalyzed Miyaura borylation/Suzuki-Miyaura cross-coupling of the C-F bond. Moreover, modular synthesis of unsymmetrical difluorinated 1,3-dienes is also achievable by the coupling between gem-difluoroalkenes and borylated monofluoroalkenes.
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