Convergent Synthesis of Fluoroalkenes Using a Dual-Reactive Unit
- 5 January 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 86 (2), 1622-1632
- https://doi.org/10.1021/acs.joc.0c02474
Abstract
Fluoroalkenes have shown importance as a metabolically stable isostere of amide compounds. To expedite the synthesis of diverse fluoroalkenes, we have developed a dual-reactive C2-unit, (Z)-1-boryl-1-fluoro-2-tosyloxyethene, containing nucleophilic and electrophilic moieties. Consecutive palladium-catalyzed cross-coupling reactions of this unit with aryl bromides and aryl boronic acids allow for the convergent synthesis of diverse trans-1,2-diaryl-substituted fluoroethenes in a chemoselective and stereoretentive manner.Keywords
Funding Information
- RIKEN
- Japan Science Society
- Japan Agency for Medical Research and Development (JP20am0101098)
- Japan Society for the Promotion of Science (JP19K16332, JP20K05521)
- Hyogo Science and Technology Association
This publication has 65 references indexed in Scilit:
- An Evaluation of Peptide‐Bond IsosteresChemBioChem, 2011
- Approaches to the preparation of (Z)-1,2-difluorostilbenesJournal of Fluorine Chemistry, 2010
- A Simple and General Platform for Generating Stereochemically Complex Polyene Frameworks by Iterative Cross‐CouplingAngewandte Chemie, 2010
- Stereoretentive Suzuki−Miyaura Coupling of Haloallenes Enables Fully Stereocontrolled Access to (−)-PeridininJournal of the American Chemical Society, 2010
- A general preparation of (Z)-1-fluorostilbene derivatives for the design of conformationally restricted peptidomimeticsTetrahedron Letters, 2010
- Asymmetric Epoxidation of Fluoroolefins by Chiral Dioxirane. Fluorine Effect on EnantioselectivityThe Journal of Organic Chemistry, 2009
- Scope of the Suzuki−Miyaura Cross-Coupling Reactions of Potassium HeteroaryltrifluoroboratesThe Journal of Organic Chemistry, 2008
- Simple, Efficient, and Modular Syntheses of Polyene Natural Products via Iterative Cross-CouplingJournal of the American Chemical Society, 2007
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995
- (E)-(2-Bromoethenyl)dibromoborane. A New Precursor for (E)-1,2-Disubstituted EthenesChemistry Letters, 1987