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C-H Bond Activation by Sulfated Zirconium Oxide is Mediated by a Sulfur-Centered Lewis Superacid.
Angew Chem Int Ed Engl
December 2024
Department of chemistry, University of California, Riverside, Riverside, CA, 92521, USA.
Sulfated zirconium oxide (SZO) catalyzes the hydrogenolysis of isotactic polypropylene (iPP, M=13.3 kDa, Đ=2.4,
Accessing Alkoxy Radicals via Frustrated Radical Pairs: Diverse Oxidative Functionalizations of Tertiary Alcohols.
J Am Chem Soc
July 2024
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.
Alkoxy radicals are versatile reactive intermediates in organic synthesis. Here, we leverage the principle of frustrated radical pair to provide convenient access to these highly reactive species directly from tertiary alcohols via oxoammonium-mediated oxidation of the corresponding alkoxides. This approach enabled various synthetically useful transformations including β-scission, radical cyclization, and remote C-H functionalization, giving rise to versatile alkoxyamines that can be further elaborated to various functionalities.
View Article and Find Full Text PDFOrganic Synthesis Away from Equilibrium: Contrathermodynamic Transformations Enabled by Excited-State Electron Transfer.
Acc Chem Res
July 2024
Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
ConspectusChemists have long been inspired by biological photosynthesis, wherein a series of excited-state electron transfer (ET) events facilitate the conversion of low energy starting materials such as HO and CO into higher energy products in the form of carbohydrates and O. While this model for utilizing light-driven charge transfer to drive catalytic reactions thermodynamically "uphill" has been extensively adapted for small molecule activation, molecular machines, photoswitches, and solar fuel chemistry, its application in organic synthesis has been less systematically developed. However, the potential benefits of these approaches are significant, both in enabling transformations that cannot be readily achieved using conventional thermal chemistry and in accessing distinct selectivity regimes that are uniquely enabled by excited-state mechanisms.
View Article and Find Full Text PDFSilver-Promoted Radical Ring-Opening/Pyridylation of Cyclobutanols with N-Methoxypyridinium Salts.
Chemistry
March 2022
Institute for Advanced and Applied Chemical Synthesis, Jinan University, Guangzhou, 510632, Guangdong, P. R. China.
The silver-promoted reaction of tertiary cyclobutanols with N-methoxypyridinium salts enables the efficient synthesis of a range of C2-substituted pyridines. The overall process likely occurs by ring-opening (via β-scission) of the cyclobutoxy radical to generate the corresponding γ-keto alkyl radical that itself adds to the pyridinium salt. A wide range of tertiary cyclobutanols and N-methoxypyridinium salts are compatible with the reaction conditions.
View Article and Find Full Text PDFPhotoinduced Ligand-to-Metal Charge Transfer (LMCT) of Fe Alkoxide Enabled C-C Bond Cleavage and Amination of Unstrained Cyclic Alcohols.
Org Lett
January 2022
School of Chemistry, MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi'an Key Laboratory of Sustainable Energy Materials Chemistry, Xi'an Jiaotong University, Xi'an 710049, P. R. China.
We report an alkoxy radical process for the C-C bond cleavage and functionalization of unstrained tertiary and secondary cyclic alcohols. In the absence of a chlorine atom, the readily available iron catalysts [Fe(OBu-) or Fe(acac)/-BuONa] facilitate alkoxy radical formation via the direct ligand-to-metal charge transfer of Fe alkoxide and further enable the ring opening and amination of cyclic alcohols. The remote amino carbonyl compounds could be obtained with a broad scope in up to excellent yields under the mildly redox-neutral system.
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