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Nickel/Photoredox Catalyzed Aryl-Alkyl Cross-Coupling with Alkyl Boronic Esters as Radical Precursors.
Chemistry
December 2024
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China.
Nickel/photoredox dual catalyzed cross-coupling of aryl halides with alkylboron compounds is one of the effective methodologies for the construction of C(sp)-C(sp) bonds. Although elegant results have been achieved by using alkyl trifluoroborates as alkyl radical precursors, the generation of alkyl radicals from readily available alkyl boronic esters is still limited due to their high oxidation potential. We disclosed here that activation of alkyl boronic esters by MeOLi is highly efficient for the generation of alkyl radicals under photocatalysis conditions.
View Article and Find Full Text PDFAminoborate-Catalyzed Reductive Counterreactions for Oxidative Electrosynthetic Transformations.
J Org Chem
December 2024
Department of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States.
Article Synopsis
- * The research introduces aminoborate adducts as effective redox mediators for proton reduction, enabling successful oxidative reactions at mild potentials, such as chlorodeborylation and Chan-Lam coupling.
- * The study highlights the benefits of using borate adducts in promoting high yields and reducing decomposition and electrode passivation, emphasizing the need for simultaneous development of both anodic and cathodic reactions in electrosynthesis.
Electrochemical Generation of Aryl Radicals from Organoboron Reagents Enabled by Pulsed Electrosynthesis.
Angew Chem Int Ed Engl
July 2024
Department of Chemistry, Northwestern University, 2145 N Sheridan Road, Evanston, IL 60208, USA.
Aryl radicals play a pivotal role as reactive intermediates in chemical synthesis, commonly arising from aryl halides and aryl diazo compounds. Expanding the repertoire of sources for aryl radical generation to include abundant and stable organoboron reagents would significantly advance radical chemistry and broaden their reactivity profile. While traditional approaches utilize stoichiometric oxidants or photocatalysis to generate aryl radicals from these reagents, electrochemical conditions have been largely underexplored.
View Article and Find Full Text PDFGold-Catalyzed C(sp)-C(sp) Suzuki-Miyaura Coupling Reaction.
Org Lett
April 2024
School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, P. R. China.
A gold-catalyzed C(sp)-C(sp) Suzuki-Miyaura coupling reaction facilitated by ligand-enabled Au(I)/Au(III) redox catalysis was developed. The cross-coupling of alkyl organometallics was first realized in the redox catalytic cycle in gold chemistry, without the use of external oxidants. This gold-catalyzed C(sp)-C(sp) coupling reaction allows a variety of alkyl chain and useful methyl trifluoroborates to react with aryl and vinyl iodides under very mild conditions, which provides a new reactivity pattern for challenging couplings with alkyl organometallics.
View Article and Find Full Text PDFOrange Light-Driven C(sp)-C(sp) Cross-Coupling via Spin-Forbidden Ir(III) Metallaphotoredox Catalysis.
J Am Chem Soc
September 2023
Department of Chemistry, Columbia University, New York, New York 10027, United States.
We report the development and characterization of a library of Ir(III) photocatalysts capable of undergoing spin-forbidden excitation (SFE) under orange light irradiation (595 nm). These catalysts were successfully applied to the construction of synthetically valuable C(sp)-C(sp) bonds inaccessible with existing methods of low-energy light-driven dual nickel/photoredox catalysis, demonstrating the synthetic utility of this photocatalyst family. The photocatalysts are capable of accessing both oxidatively and reductively activated coupling partners, illustrated through deaminative arylation and potassium alkyl trifluoroborate cross-coupling reactions with aryl halides.
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