- Integrating Organic Lewis Acid and Redox Catalysis: The Phenalenyl Cation in Dual Role
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In recent years, merging different types of catalysis in a single pot has drawn considerable attention and these catalytic processes have mainly relied upon metals. However, development of a completely metal free approach integrating organic redox and organic Lewis acidic property into a single system has been missing in the current literature. This study establishes that a redox active phenalenyl cation can activate one of the substrates by single electron transfer process while the same can activate the other substrate by a donor-acceptor type interaction using its Lewis acidity. This approach has successfully achieved light and metal-free catalytic C-H functionalization of unactivated arenes at ambient temperature (39 entries, including core moiety of a top-selling molecule boscalid), an economically attractive alternative to the rare metal-based multicatalysts process. A tandem approach involving trapping of reaction intermediates, spectroscopy along with density functional theory calculations unravels the dual role of phenalenyl cation.
- Ahmed, Jasimuddin,Chakraborty, Soumi,Jose, Anex,Sreejyothi,Mandal, Swadhin K.
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supporting information
p. 8330 - 8339
(2018/06/19)
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- Ligand-Promoted Direct C-H Arylation of Simple Arenes: Evidence for a Cooperative Bimetallic Mechanism
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A highly efficient catalyst for the direct C-H arylation of simple arenes was developed on the basis of a palladium-diimine complex. The developed catalyst exhibited the highest turnover number reported to date for the direct arylation of benzene due to increased stability provided by the diimine ligand. The reaction was also performed using only 2-3 equiv of simple arenes. Mechanistic studies in combination with kinetic measurements, isotope effect experiments, synthesis of possible intermediates, and stoichiometric reactions suggested that this reaction follows a cooperative bimetallic mechanism.
- Kim, Jaewoon,Hong, Soon Hyeok
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p. 3336 - 3343
(2017/06/09)
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- Decarboxylative biaryl synthesis in a continuous flow reactor
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A practical protocol was developed that allows performing decarboxylative cross-coupling reactions in continuous flow reactors. Various biaryls were thus synthesized from aromatic carboxylic acids and aryl triflates using a Cu/Pd-catalyst system.
- Lange, Paul P.,Goossen, Lukas J.,Podmore, Philip,Underwood, Toby,Sciammetta, Nunzio
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supporting information; scheme or table
p. 3628 - 3630
(2011/05/02)
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- A new palladium catalyzed protocol for atom-efficient cross-coupling reactions of?triarylbismuths with aryl halides and triflates
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A new palladium catalyzed protocol for an atom-efficient cross-coupling reaction of triarylbismuths with aryl halides and triflates has been described. The palladium catalytic system with Cs2CO3 base was found to be very efficient in DMA solvent to furnish excellent yields of cross-coupled functionalized biaryls in short reaction times.
- Rao, Maddali L.N.,Jadhav, Deepak N.,Banerjee, Debasis
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p. 5762 - 5772
(2008/09/21)
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- Preparation of unsymmetrical biaryls via palladium-catalyzed coupling reaction of aryl halides
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The synthesis of unsymmetrical biaryls is achieved using Pd(OAc)2 as the catalyst. A great variety of aryl halides having electron withdrawing and electron donating functional groups in para, meta and ortho positions have been successfully coupled.
- Hassan, Jwanro,Hathroubi, Chokri,Gozzi, Christel,Lemaire, Marc
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p. 7845 - 7855
(2007/10/03)
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- Direct Conversion of Arylamines to the Corresponding Halides, Biphenyls, and Sulfides with t-Butyl Thionitrate
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t-Butyl thionitrate have been found to be an excellent diazotizing reagent of arylamines in aprotic nonpolar media, affording eventually such products as aryl chlorides, aryl bromides, aryl iodides, biphenyls, and aryl methyl sulfides in the presence of CCl4, CHBr3, I2, benzene, and dimethyl disulfide, respectively, via extrusion of N2.
- Oae, Shigeru,Shinhama, Koichi,Kim, Yong Hae
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p. 2023 - 2026
(2007/10/02)
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