Hexafluoroisopropanol as a highly versatile solvent
Ignacio Colomer,Anna E. R. Chamberlain,Maxwell B. Haughey,Timothy J. Donohoe +3 more
- 08 Nov 2017
- Vol. 1, Iss: 11, pp 1-12
TL;DR: In this paper, the main uses of hexafluoroisopropanol (HFIP) in the natural sciences and the underlying principles that give it such wide appeal are discussed. And the broad usage and beneficial effects in many areas of chemistry are shown.
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Abstract: 1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) has recently become a very popular solvent or additive with applications across the spectrum of chemistry. Analysis shows that it possesses a wide range of interesting and unique properties. In this Perspective, we detail the main uses of HFIP in the natural sciences and disclose the underlying principles that give it such wide appeal. Accordingly, we show the broad usage and beneficial effects in many areas of chemistry. Reviewing the applications of a solvent would ordinarily be an unusual thing to do, but the unique properties of hexafluoroisopropanol and its applications across a huge swathe of chemistry make that both a viable and interesting undertaking.
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Figures
Figure 5: Selected examples of organometallic species used in combination with HFIP. a) Metal-catalysed C-H activation; b) non-classical hydrogen bonding between HFIP and transition metal complexes. 
Figure 1: Use of HFIP with H2O2 in: a) Baeyer-Villiger oxidation of ketones. b epoxidation of 
Figure 3: Selected metal-free C–H bond activation employing HFIP as a solvent. The use of fluorinated solvents in C–H bond activation processes, particularly HFIP, has become increasingly common in recent years, a) Photoinduced dual borylation of haloarenes; b) Organocatalytic C(sp 3 )–H hydroxylation 
Figure 4: Selected oxidative C–H and N-H bond functionalization employing HFIP as a solvent. The use of HFIP in electrochemical processes has become increasingly common in recent years, for example in a) C–H oxidative homo- and cross-coupling of phenols; b) N-H oxidative coupling.
Citations
Three-component aminofluorination of alkenes with electronically rich amino sources
Yang Li,Jiamin Bao,Yu Zhang,Xue Peng,Weijie Yu,Tao Wang,Den-Kai Yang,Qun Liu,Xiang Zhang,Junkai Fu +9 more
TL;DR: The first intermolecular three-component aminofluorination of alkenes with electronically rich amino sources has been developed via an umpolung strategy in this article .
Unusual Overhauser Dynamic Nuclear Polarization Behavior of Fluorinated Alcohols at Room Temperature
Arnab Dey,Abhishek Banerjee +1 more
TL;DR: It is shown that 1H and 19F Overhauser Dynamic Nuclear Polarization (ODNP) build-up curves in solution state at room temperature show unusual behavior that could offer a novel approach to investigate the structural heterogeneity and dynamics of such homogeneous liquids with improved sensitivity.
The Oxidation of Electron-Rich Arenes Using a H<sub>2</sub>O<sub>2</sub>–Proline System
Lloyd C. Chetty,Hendrik G. Kruger,Per I. Arvidsson,Glenn E. M. Maguire,Thavendran Govender,Tricia Naicker +5 more
TL;DR: A novel proline-catalyzed oxidation system using H2O2 synthesizes quinones from diverse substrates with moderate-to-high yields, adhering to green chemistry principles, and offering a cost-effective, metal-free, and environmentally benign approach with short reaction times.
Pushing the boundaries of C–H bond functionalization chemistry using flow technology
TL;DR: An up-to-date overview of C-H bond functionalization reactions carried out in continuous-flow microreactors is presented in this article, where a comprehensive overview of reactions which establish the formal conversion of a C−H bond into carbon-carbon or carbon-heteroatom bonds is provided.
Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products.
TL;DR: A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described, and the corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings.
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