56441-91-9Relevant articles and documents
One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride
Epifanov, Maxim,Mo, Jia Yi,Dubois, Rudy,Yu, Hao,Sammis, Glenn M.
, p. 3768 - 3777 (2021/03/01)
Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.
Alkene Hydrogenations by Soluble Iron Nanocluster Catalysts
Gieshoff, Tim N.,Chakraborty, Uttam,Villa, Matteo,Jacobi von Wangelin, Axel
, p. 3585 - 3589 (2017/03/21)
The replacement of noble metal technologies and the realization of new reactivities with earth-abundant metals is at the heart of sustainable synthesis. Alkene hydrogenations have so far been most effectively performed by noble metal catalysts. This study reports an iron-catalyzed hydrogenation protocol for tri- and tetra-substituted alkenes of unprecedented activity and scope under mild conditions (1–4 bar H2, 20 °C). Instructive snapshots at the interface of homogeneous and heterogeneous iron catalysis were recorded by the isolation of novel Fe nanocluster architectures that act as catalyst reservoirs and soluble seeds of particle growth.
Synthesis of oxygen- and sulfur-bridged dirhodium complexes and their use as catalysts in the chemoselective hydrogenation of alkenes
Zhu, Chuan,Yukimura, Noriaki,Yamane, Motoki
experimental part, p. 2098 - 2103 (2010/06/19)
Oxygen-bridged and sulfur-bridged rhodium homobimetallic complexes were synthesized as air-stable crystals by using 2,6-bis(phosphanylmethyl)phenolate and -thiophenolate as the ligands, respectively. The oxygen-bridged dirhodium complex has a symmetrical structure where the carbon atom at the ipso position, oxygen, and two rhodium atoms are located in the same plane. It is thermally stable compared to the sulfur-bridged dirhodium complex and shows catalytic activity for hydrogenation of alkenes with high chemoselectivity.