2248-13-7Relevant articles and documents
Access to Trisubstituted Fluoroalkenes by Ruthenium-Catalyzed Cross-Metathesis
Nouaille, Augustin,Pannecoucke, Xavier,Poisson, Thomas,Couve-Bonnaire, Samuel
supporting information, p. 2140 - 2147 (2021/03/06)
Although the olefin metathesis reaction is a well-known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross-Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post-functionalizable source of fluoroalkene, that we found as the methyl 2-fluoroacrylate. We reported herein the efficient ruthenium-catalyzed CM reaction of various terminal and internal alkenes with methyl 2-fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products. (Figure presented.).
Phosphorus Coordination Chemistry in Catalysis: Air Stable P(III)-Dications as Lewis Acid Catalysts for the Allylation of C-F Bonds
Chitnis, Saurabh S.,Lafortune, James H. W.,Cummings, Haley,Liu, Liu Leo,Andrews, Ryan,Stephan, Douglas W.
supporting information, p. 4540 - 4544 (2019/01/08)
Modification of C-F bonds with main-group catalysts has typically employed electron-deficient Lewis superacids in high oxidation states, and the challenges of preparing and handling such species have prevented broader adoption of metal-free reduction protocols. Here, we show that a hemilabile ligand coordinated to an easily accessed P(III) center imparts air stability without sacrificing the ability to activate C-F bonds. Catalytic C-C coupling of benzyl fluorides with allylsilanes was achieved using a P(III) complex under benchtop conditions. This application of coordination chemistry principles to main-group Lewis acids reveals a new strategy for controlling catalysis.
Palladium-Catalyzed Electrochemical Allylic Alkylation between Alkyl and Allylic Halides in Aqueous Solution
Lai, Yin-Long,Huang, Jing-Mei
supporting information, p. 2022 - 2025 (2017/04/28)
A new route for the direct cross-coupling of alkyl and allylic halides using electrochemical technique has been developed in aqueous media under air. Catalyzed by Pd(OAc)2, the Zn-mediated allylic alkylations proceed smoothly between a full range of alkyl halides (primary, secondary, and tertiary) and substituted allylic halides. Protection-deprotection of acidic hydrogen in the substrates is avoided.