Hoch effiziente C‐SeCF<sub>3</sub>‐Kupplung von Aryliodiden durch einen luftbeständigen zweikernigen Pd<sup>I</sup>‐Katalysator

Aufiero, Marialuisa; Sperger, Theresa; Tsang, Althea S.‐K.; Schoenebeck, Franziska

doi:10.1002/ange.201503388

Cited by 62 publications

(4 citation statements)

References 74 publications

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“…Inspired by the efficient dinuclear Pd I catalyzed trifluoromethylthiolation mentioned above, Schoenebeck and co-workers then investigated the first catalytic trifluoromethylselenolation of aryl iodides. [23] The illustrated X-ray structure of complex C (X=Se) proved the feasible exchange of I to SeCF 3 anion. A number of aryl iodides bearing either electron-withdrawing or -donating moieties were converted into the desired trifluoromethylselenolation products 4 in moderate to excellent yields.…”

Section: Palladium-catalyzed Trifluoromethylthiolation and Trifluorommentioning

confidence: 94%

“…The computational studies suggested that the reaction proceeded by oxidative addition of both complex B and C to D, and final products were then obtained by the following reductive elimination process. Inspired by the efficient dinuclear Pd I catalyzed trifluoromethylthiolation mentioned above, Schoenebeck and co‐workers then investigated the first catalytic trifluoromethylselenolation of aryl iodides [23] . The illustrated X‐ray structure of complex C (X=Se) proved the feasible exchange of I to SeCF 3 anion.…”

Section: Transition‐metal‐catalyzed Trifluoromethylthiolation and Tri...mentioning

confidence: 99%

“…Pd I -catalyzed trifluoromethylthiolation of aryl iodides and bromides with (Me 4 N)SCF 3 , and Pd I -catalyzed trifluoromethylselenolation of aryl iodides with (Me 4 N)SeCF 3 . [21,23] Scheme 2. Ni 0 -catalyzed trifluoromethylthiolation of aryl iodides and bromides with (Me 4 N)SCF 3 .…”

Section: Nickel-catalyzed Trifluoromethylthiolation and Trifluorometh...mentioning

confidence: 99%

“… Pd I ‐catalyzed trifluoromethylthiolation of aryl iodides and bromides with (Me 4 N)SCF 3 , and Pd I ‐catalyzed trifluoromethylselenolation of aryl iodides with (Me 4 N)SeCF 3 [21,23] …”

Section: Transition‐metal‐catalyzed Trifluoromethylthiolation and Tri...mentioning

confidence: 99%

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Recent Advances and Uses of (Me₄N)XCF₃ (X=S, Se) in the Synthesis of Trifluoromethylthiolated and Trifluoromethylselenolated Compounds

et al. 2020

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The introduction of trifluoromethylthio (SCF 3) and trifluoromethylseleno (SeCF 3) substituents into organic molecules significantly improves the electron-withdrawing and lipophilic properties of their parent compounds. Therefore, a vast class of versatile reagents were employed to access the corresponding fluorine-containing compounds. Among them, tetramethylammonium salts, such as (Me 4 N)SCF 3 and (Me 4 N) SeCF 3 , have been employed as practical and efficient non-metal reagents for developing efficient trifluoromethylthiolation and trifluoromethylselenolation in recent years. This Minireview systematically illustrates the application of (Me 4 N)XCF 3 (X=S, Se) in the synthesis of trifluoromethylthiolated and trifluoromethylselenolated compounds, and its content is divided into two categories: transition-metalcatalyzed reactions, and transition-metal-free reactions. Scheme 13. Metal-free trifluoromethylthiolation and trifluoromethylselenolation of alkynyl(phenyl) iodoniums with (Me 4 N)SCF 3 and (Me 4 N) SeCF 3. [45] Scheme 14. Metal-free trifluoromethylthiolation of arenediazonium salts with (Me 4 N)SCF 3. [46] Scheme 15. Catalyst-and additive-free trifluoromethylselenolation of organic halides, diaryliodonium triflate, aryldiazonium tetrafluoroborates and αdiazo carbonyls with (Me 4 N)SeCF 3. [49] Scheme 16. Metal-free trifluoromethylthiolation of cyclic sulfamidates with (Me 4 N)SCF 3. [50] Minireview 69

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Section: Palladium-catalyzed Trifluoromethylthiolation and Trifluorommentioning

confidence: 94%

Section: Transition‐metal‐catalyzed Trifluoromethylthiolation and Tri...mentioning

confidence: 99%

Section: Nickel-catalyzed Trifluoromethylthiolation and Trifluorometh...mentioning

confidence: 99%

Section: Transition‐metal‐catalyzed Trifluoromethylthiolation and Tri...mentioning

confidence: 99%

See 2 more Smart Citations

Recent Advances and Uses of (Me₄N)XCF₃ (X=S, Se) in the Synthesis of Trifluoromethylthiolated and Trifluoromethylselenolated Compounds

et al. 2020

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Copper‐Catalyzed Direct Trifluoro‐ and Perfluoroalkylselenolations of Boronic Acids with a Shelf‐Stable Family of Reagents

et al. 2017

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Herein the copper‐catalyzed direct perfluoroalkylselenolation of aryl‐ and vinylboronic acids is described for the first time. The key to success is the design of new shelf‐stable perfluoroalkylselenolating reagents, namely perfluoroalkyl tolueneselenosulfonates. The reaction occurs at room temperature in the presence of commercially available catalyst and ligand in catalytic quantities.magnified image

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Ligand‐Controlled C−O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights

Song

Zhong

et al. 2019

Adv Synth Catal

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Palladium‐catalyzed cross‐coupling reactions between carboxylic acids and aryl halides have several possible competitive pathways. Decarboxylative C−C bond coupling and C−H arylation are well established in the literature. However, direct C−O bond coupling between carboxylic acids and aryl halides has received little success. In this report, we describe a protocol for exclusive C−O bond formation, enabled by a bidentate N,N‐ligand such as 1,10‐phenanthroline. The reaction is general for a broad range of carboxylic acids and iodoarenes. Experimental evidence and computational results suggest a high energy barrier for the alternative pathway of decarboxylative carbon‐carbon bond coupling.

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Hoch effiziente C‐SeCF₃‐Kupplung von Aryliodiden durch einen luftbeständigen zweikernigen Pd^I‐Katalysator

Cited by 62 publications

References 74 publications

Recent Advances and Uses of (Me₄N)XCF₃ (X=S, Se) in the Synthesis of Trifluoromethylthiolated and Trifluoromethylselenolated Compounds

Recent Advances and Uses of (Me₄N)XCF₃ (X=S, Se) in the Synthesis of Trifluoromethylthiolated and Trifluoromethylselenolated Compounds

Copper‐Catalyzed Direct Trifluoro‐ and Perfluoroalkylselenolations of Boronic Acids with a Shelf‐Stable Family of Reagents

Ligand‐Controlled C−O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights

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Hoch effiziente C‐SeCF3‐Kupplung von Aryliodiden durch einen luftbeständigen zweikernigen PdI‐Katalysator

Cited by 62 publications

References 74 publications

Recent Advances and Uses of (Me4N)XCF3 (X=S, Se) in the Synthesis of Trifluoromethylthiolated and Trifluoromethylselenolated Compounds

Recent Advances and Uses of (Me4N)XCF3 (X=S, Se) in the Synthesis of Trifluoromethylthiolated and Trifluoromethylselenolated Compounds

Copper‐Catalyzed Direct Trifluoro‐ and Perfluoroalkylselenolations of Boronic Acids with a Shelf‐Stable Family of Reagents

Ligand‐Controlled C−O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights

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Resources

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Hoch effiziente C‐SeCF₃‐Kupplung von Aryliodiden durch einen luftbeständigen zweikernigen Pd^I‐Katalysator

Recent Advances and Uses of (Me₄N)XCF₃ (X=S, Se) in the Synthesis of Trifluoromethylthiolated and Trifluoromethylselenolated Compounds

Recent Advances and Uses of (Me₄N)XCF₃ (X=S, Se) in the Synthesis of Trifluoromethylthiolated and Trifluoromethylselenolated Compounds