123005-21-0Relevant articles and documents
Photo-Induced Cross-Dehydrogenative Alkylation of Heteroarenes with Alkanes under Aerobic Conditions
Xu, Jun,Cai, Heng,Shen, Jiabin,Shen, Chao,Wu, Jie,Zhang, Pengfei,Liu, Xiaogang
, p. 17816 - 17832 (2021/12/17)
We report a Minisci-type cross-dehydrogenative alkylation in an aerobic atmosphere using abundant and inexpensive cerium chloride as a photocatalyst and air as an oxidant. This photoreaction exhibits excellent tolerance to functional groups and is suitabl
Metal-free radical-mediated C(sp3)-H heteroarylation of alkanes
Shao, Xin,Wu, Shuo,Wu, Xinxin,Zhu, Chen
supporting information, p. 7450 - 7454 (2020/11/02)
Herein we disclose a metal-free, N/O-centered radical-promoted Minisci reaction, in which the coupling of various heteroarenes with simple alkanes proceeds under mild conditions. The reaction conditions are neutral; no extra acid is added to preactivate N
Visible Light-Promoted Aliphatic C-H Arylation Using Selectfluor as a Hydrogen Atom Transfer Reagent
Zhao, Hong,Jin, Jian
supporting information, p. 6179 - 6184 (2019/09/06)
A mild, practical method for direct arylation of unactivated C(sp3)-H bonds with heteroarenes has been achieved via photochemistry. Selectfluor is used as a hydrogen atom transfer reagent under visible light irradiation. A diverse range of chem
Organocatalyzed, Visible-Light Photoredox-Mediated, One-Pot Minisci Reaction Using Carboxylic Acids via N-(Acyloxy)phthalimides
Sherwood, Trevor C.,Li, Ning,Yazdani, Aliza N.,Dhar, T. G. Murali
, p. 3000 - 3012 (2018/03/09)
An improved, one-pot Minisci reaction has been developed using visible light, an organic photocatalyst, and carboxylic acids as radical precursors via the intermediacy of in situ-generated N-(acyloxy)phthalimides. The conditions employed are mild, demonstrate a high degree of functional group tolerance, and do not require a large excess of the carboxylic acid reactant. As a result, this reaction can be applied to drug-like scaffolds and molecules with sensitive functional groups, enabling late-stage functionalization, which is of high interest to medicinal chemistry.
Versatile cross-dehydrogenative coupling of heteroaromatics and hydrogen donors via decatungstate photocatalysis
Quattrini, Matteo C.,Fujii, Saki,Yamada, Keiichi,Fukuyama, Takahide,Ravelli, Davide,Fagnoni, Maurizio,Ryu, Ilhyong
supporting information, p. 2335 - 2338 (2017/02/23)
A facile sunlight-induced derivatization of heteroaromatics via photocatalyzed C-H functionalization in amides, ethers, alkanes and aldehydes is described. Tetrabutylammonium decatungstate (TBADT) was used as the photocatalyst and allowed to carry out the
Direct selective oxidative cross-coupling of simple alkanes with heteroarenes
Antonchick, Andrey P.,Burgmann, Lars
supporting information, p. 3267 - 3271 (2013/04/10)
A dream reaction: An efficient and practical method for the oxidative cross-coupling of heteroaromatic compounds and simple alkanes has been developed. The desired products are smoothly and regioselectively formed under mild reaction conditions at ambient temperature in a hypervalent-iodine-mediated transformation. The method allows for preferential transformation of stronger C sp 3-H bonds in the presence of weaker C sp 3-H bonds under metal-free conditions.
Homolytic alkylation of heteroaromatic bases : The problem of monoalkylation
Fontana,Minisci,Barbosa, M. C. Nogueira,Vismara
, p. 2525 - 2538 (2007/10/02)
The silver-catalyzed decarboxylation of carboxylic acids by persulphate leads to alkyl radicals, which have been utilized for the selective alkylation of heteroaromatic bases. The method is particularly efficient in a water-chlorobenzene two-phase system for two reasons : it considerably increases the selectivity in monoalkylation when more positions of high nucleophilic reactivity (i.e. α and γ) are available in the heterocyclic ring (i.e. quinoline , 4-cyano- and 4-ethylpyridine, pyrazine , quinoxaline etc.) and it determines a much higher efficiency for the radical sources when the silver salt catalysis is deactivated by complexation of the salt with the heterocyclic compound . The high selectivity in monoalkylation has been obtained by the combination of polar effects and the increased lipophilicity of the alkylated product, which makes its extraction from the aqueous solution by the organic solvent easier.
New General Processes of Homolytic Alkylation of Heteroaromatic Bases by t-BuOOH or (t-BuO)2 and Alkyl Iodides
Fontana, Francesca,Minisci, Francesco,Barbosa, Maria Claudia Nogueira,Vismara, Elena
, p. 995 - 999 (2007/10/02)
New general, selective processes of homolytic alkylation of protonated heteroaromatic bases have been developed using alkyl iodides and t-BuOOH or (t-BuO)2 as sources of alkyl radicals.Both processes are based on the generation of methyl radical from the peroxides, and on iodine abstraction from the alkyl iodide by the methyl radical.The selective processes are the result of combined enthalpic and polar effects.The enthalpic factor governs the equilibrium of iodine abstraction, whereas the polar effect governs the reactivity of the alkyl radicals with the protonated heteroaromatic ring.A redox chain is operative with t-BuOOH and an unusual free-radical chain process is involved with (t-BuO)2.Both chains are particularly effective because of the electron-transfer oxidation of the pyridyl radical intermediate, the ionization potential of which (5.4-6.0 eV) is close to that of lithium (5.39 eV) or sodium (5.14 eV).
