- A Unified and Practical Method for Carbon–Heteroatom Cross-Coupling using Nickel/Photo Dual Catalysis
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While carbon–heteroatom cross-coupling reactions have been extensively studied, many methods are specific and limited to a particular set of substrates or functional groups. Reported here is a general method that allows for C?O, C?N and C?S cross-coupling reactions under one general set of conditions. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel(II) complex, is responsible for the key reductive elimination step that couples aryl bromides, iodides, and chlorides to 1° and 2° alcohols, amines, thiols, carbamates, and sulfonamides, and is amenable to scale up via a flow apparatus.
- Escobar, Randolph A.,Johannes, Jeffrey W.
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supporting information
(2020/04/17)
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- Palladium-Catalyzed 2,2,2-Trifluoroethoxylation of Aromatic and Heteroaromatic Chlorides Utilizing Borate Salt and the Synthesis of a Trifluoro Analogue of Sildenafil
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A simple and convenient method was developed for the introduction of a 2,2,2-trifluoroethoxy group to various aromatic and heteroaromatic systems. The novel process utilizes aromatic chlorides as substrates, and tetrakis(2,2,2-trifluoroethoxy) borate salt as an inexpensive and readily available fluoroalkoxy source in a palladium-catalyzed cross-coupling reaction. The power of the developed methodology was demonstrated in the synthesis of a fluorous derivative of Sildenafil.
- Peth?, Bálint,Zwillinger, Márton,Csenki, János T.,Káncz, Anna E.,Krámos, Balázs,Müller, Judit,Balogh, Gy?rgy T.,Novák, Zoltán
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supporting information
p. 15628 - 15632
(2017/10/20)
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- Facile and efficient synthesis of fluoroalkyl aryl ethers
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A convenient and practical method for the preparation of fluoroalkyl aryl ethers via substitution of iodoalkyl fluorides is described. This method involves KF complexation of the phenol, which increases the nucleophilicity of oxygen for the formation of the ether linkage.
- Kamal, Ahmed,Pratap,Ramana, K.Venkata,Ramana,Babu, A.Hari
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p. 7353 - 7355
(2007/10/03)
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- Aromatic Fluoroalkoxylation via Direct Aromatic Nucleophilic Substitution
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The reaction of activated aryl and heteroaryl halides with fluorinated alkoxide anions is described.In all cases, substitution of the halogen by a fluoroalkoxy group was observed.The effect of solvent, time, temperature, the activating group, leaving group, and the nucleophile on this reaction is also discussed.
- Idoux, John P.,Gupton, John T.,McCurry, Cynthia K.,Crews, A. Donald,Jurss, Cindy D.,et al.
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p. 3771 - 3773
(2007/10/02)
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