Transition‐Metal‐Free Oxidative Cross‐Coupling of Tetraarylborates to Biaryls Using Organic Oxidants

Gerleve, Carolin; Studer, Armido

doi:10.1002/anie.202002595

Cited by 41 publications

(26 citation statements)

References 71 publications

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“…The biphenyl product was characterized by 1 H NMR and GC, and agreement with the literature data. [59][60][61][62][63]…”

Section: General Methods For the Synthesis Of Substituted Schiff Basesmentioning

confidence: 99%

Synthesis of new Schiff bases; Investigation of their in situ catalytic activity for Suzuki CC coupling reactions and antioxidant activities

Yılmaz

2021

J Chinese Chemical Soc

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New series of Schiff bases have been synthesized from the reaction between cyclohepta-2,4,6-trien-1-ylmethanamine and different aldehydes, and characterized via using 1 H NMR, 13 C NMR, FTIR spectroscopy, and GC-MS. After the successful synthesis, the in situ catalytic activity of all Schiff bases have been examined for the Suzuki C C cross-coupling reactions using phenylboronic acid, aryl bromides, and PdCl 2 as a catalyst. Before starting these investigations, reaction conditions were optimized using different bases and solvents. At the end of these reactions, the best efficiency was obtained in Et 3 N and EtOH. In addition to catalytic investigations, antioxidant activities of all synthesized Schiff bases were examined using DPPH and Iron (Fe 2+ ) chelation methods, and IC 50 values were calculated. While many molecules show various amounts of antioxidant activity, especially molecules 8e and 8g showed the best activity compared to butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA), which were used as positive controls, in DPPH and Iron chelating methods, respectively.

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“…The biphenyl product was characterized by 1 H NMR and GC, and agreement with the literature data. [59][60][61][62][63]…”

Section: General Methods For the Synthesis Of Substituted Schiff Basesmentioning

confidence: 99%

Synthesis of new Schiff bases; Investigation of their in situ catalytic activity for Suzuki CC coupling reactions and antioxidant activities

Yılmaz

2021

J Chinese Chemical Soc

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“…The formation of the ammonia protected triarylboranes 3 a – g via addition of various organomagnesium on the 9‐aminoethoxy‐9,10‐dihydro‐boraanthracene 2 was next investigated (Scheme 4). Our initial experimental conditions were based on an example reported by Shaver on a similar Ar 2 B(ethanolamine) derivative [7b, g] …”

Section: Resultsmentioning

confidence: 99%

Methylene Bridging Effect on the Structures, Lewis Acidities and Optical Properties of Semi‐planar Triarylboranes

Doan

Chardon

Osi

et al. 2020

Chemistry A European J

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Three synthetic methods towards semi‐planar triarylboranes with two aryl rings connected by a methylene bridge have been developed. The fine‐tuning of their stereoelectronic properties and Lewis acidities was achieved by introducing fluorine, methyl, methoxy, n‐butyl and phenyl groups either at their exocyclic or bridged aryl rings. X‐ray diffraction analysis and quantum‐chemical calculations provided quantitative information on the structural distortion experienced by the near planar hydro‐boraanthracene skeleton during the association with Lewis bases such as NH3 and F−. Though the methylene bridge between the ortho‐positions of two aryl rings of triarylboranes decreased the Gibbs free energies of complexation with small Lewis bases by less than 5 kJ mol−1 relative to the classical Lewis acid BAr3, the steric shielding of the CH2 bridge is sufficient to avoid the formation of Lewis adducts with larger Lewis bases such as triarylphosphines. A newly synthesized spirocyclic amino‐borane with a long intramolecular B−N bond that could be dissociated under thermal process, UV‐irradiation, or acidic conditions might be a potential candidate in Lewis pairs catalysis.

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“…Building on methodologies developed in our group to access functionalized organoboron derivatives, we recently demonstrated an efficient and chemoselective electrochemical synthesis of unsymmetrical biaryls [13] and heteroarylated olefins [14] from readily accessible tetraorganoborate salts (TOBs). The group of Studer similarly reported an elegant chemical oxidation of mixed tetraorganoborates towards hetero‐biaryls using Bobbitt's salt [15] …”

Section: Methodsmentioning

confidence: 99%

Photocatalyzed Transition‐Metal‐Free Oxidative Cross‐Coupling Reactions of Tetraorganoborates**

Music

Baumann

Boser

et al. 2021

Chemistry A European J

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Readily accessible tetraorganoborate salts undergo selective coupling reactions under blue light irradiation in the presence of catalytic amounts of transition‐metal‐free acridinium photocatalysts to furnish unsymmetrical biaryls, heterobiaryls and arylated olefins. This represents an interesting conceptual approach to forge C−C bonds between aryl, heteroaryl and alkenyl groups under smooth photochemical conditions. Computational studies were conducted to investigate the mechanism of the transformation.

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Transition‐Metal‐Free Oxidative Cross‐Coupling of Tetraarylborates to Biaryls Using Organic Oxidants

Cited by 41 publications

References 71 publications

Synthesis of new Schiff bases; Investigation of their in situ catalytic activity for Suzuki CC coupling reactions and antioxidant activities

Synthesis of new Schiff bases; Investigation of their in situ catalytic activity for Suzuki CC coupling reactions and antioxidant activities

Methylene Bridging Effect on the Structures, Lewis Acidities and Optical Properties of Semi‐planar Triarylboranes

Photocatalyzed Transition‐Metal‐Free Oxidative Cross‐Coupling Reactions of Tetraorganoborates**

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